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5300-03-8 molecular structure
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3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

ChemBase ID: 635
Molecular Formular: C20H28O2
Molecular Mass: 300.43512
Monoisotopic Mass: 300.20893014
SMILES and InChIs

SMILES:
OC(=O)C=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C
Canonical SMILES:
CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
InChI:
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)
InChIKey:
SHGAZHPCJJPHSC-UHFFFAOYSA-N

Cite this record

CBID:635 http://www.chembase.cn/molecule-635.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2Z,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
IUPAC Traditional name
tretinoin
isotretinoin
11-cis-retinoic acid
(2Z,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
9,13-di-cis-retinoic acid
Brand Name
Aberel
Accutane
Airol
Aknefug
Aknoten
Amnesteem
Claravis
Dermairol
Eudyna
Lsotretinoin
Retisol-A
Solage
Sotret
Stieva-A
Stieva-a Forte
Tri-Luma
Vitinoin
Atra-IV
Accutane Roche
Synonyms
ATRA
Retionic Acid
All Trans-Retinoic Acid
All Trans Retinoic Acid
beta-Retinoic Acid
tretinoin
Tretinoin
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
RA
Retinoic acid
13-cis-Retinoic acid
all-trans-Retinoic acid
Retinoic acid
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2Z,4E,6E,8E-nonatetranenoic Acid
13-cis-Vitamin A Acid
Isotrex
IsotrexGel
Neovitamin A Acid
Ro 4-3780
Roaccutan
Roaccutane
(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid
Aberel
Avita
Retinova
11-cis-Retinoic Acid
11-cis-Retinoic Acid
(11-cis,13-cis)-Retinoic Acid
11,13-Di-cis-retinoic Acid
11-cis,13-cis-Retinoic Acid
all-trans-Retinoic Acid
(9-cis,13-cis)-Retinoic Acid
9,13-Di-cis-retinoic Acid
9-cis,13-cis-Retinoic Acid
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Isotretinoin
13-cis-RETINOIC ACID
Vitamin A acid
RETINOIC ACID ALL trans ISOMER
9-cis-RETINOIC ACID
Accutane
Amnesteem
Claravis
Sotret
Airol
Renova
Atralin
Retin-A
Av
Vesanoid
Isotretinoin
视黄酸
CAS Number
5300-03-8
4759-48-2
302-79-4
68070-35-9
5352-74-9
3555-80-4
EC Number
206-129-0
225-296-0
MDL Number
MFCD00079542
MFCD00001551
Beilstein Number
2057223
Merck Index
148165
PubChem SID
24278674
160964098
24278676
46504843
PubChem CID
444795
5538
CHEMBL
38
Wikipedia Title
Retinoic_acid

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Donor LogD (pH = 5.5) 4.392896 
LogD (pH = 7.4) 2.6406298  Log P 5.0143676 
Molar Refractivity 97.7908 cm3 Polarizability 36.17498 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five false  Acid pKa 4.996648 
H Acceptors
Log P 5.66  LOG S -4.8 
Solubility (Water) 4.77e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
<0.1 g/100 mL expand Show data source
Acetone expand Show data source
Chloroform expand Show data source
Dimethyl Sulfoxide (25mg/ml) expand Show data source
DMSO expand Show data source
Ethanol (25 mg/ml) expand Show data source
Ethanol (slightly) expand Show data source
Ether expand Show data source
Ethyl Acetate expand Show data source
Isopropanol expand Show data source
Methanol expand Show data source
nearly insoluble in water expand Show data source
soluble in fat expand Show data source
Apperance
Crystalline expand Show data source
Pale Yellow Solid expand Show data source
yellow powder expand Show data source
yellow to light orange crystalline powder with characteristic floral odor expand Show data source
Yellow-Orange Solid expand Show data source
Melting Point
116-120°C expand Show data source
168-170°C expand Show data source
172-175 °C(lit.) expand Show data source
176-178°C expand Show data source
180-181 °C(lit.) expand Show data source
180-182 °C, crystals from ethanol expand Show data source
180-182°C expand Show data source
180-182°C expand Show data source
182-186 °C expand Show data source
89-92°C expand Show data source
Hydrophobicity(logP)
4.2 expand Show data source
Storage Condition
0°C, Desiccate, Protect from light expand Show data source
-20°C expand Show data source
-20°C, Protect from light expand Show data source
-20°C, Store Under Nitrogen, Protect from light expand Show data source
-86°C Freezer, Under Inert Atmosphere expand Show data source
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
Amber Vial, -86°C Freezer, Under Inert Atmosphere expand Show data source
Storage Warning
IRRITANT expand Show data source
Light Sensitive expand Show data source
Moisture, Temperature, Light Sensitive, Store in freezer expand Show data source
Store Dry in Freezer at -20°C for up to 1 year; in Solution expand Show data source
RTECS
VH6440000 expand Show data source
VH6475000 expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Risk Statements
22 expand Show data source
22-51/53 expand Show data source
22-63 expand Show data source
61-36/37/38 expand Show data source
R:22 expand Show data source
Safety Statements
36/37 expand Show data source
53-26-36/37/39-45 expand Show data source
61 expand Show data source
S:36/37/39 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H301-H361 expand Show data source
H302 expand Show data source
H302-H411 expand Show data source
H315-H319-H335-H360 expand Show data source
GHS Precautionary statements
P201-P261-P305 + P351 + P338-P308 + P313 expand Show data source
P273 expand Show data source
P281-P301+P310-P321-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Target
hydroxysteroid dehydrogenase expand Show data source
Gene Information
human ... NOS2(4843), RARA(5914), RARB(5915) expand Show data source
human ... RARA(5914), RARB(5915), RARG(5916) expand Show data source
human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)mouse ... Rara(19401), Rarb(218772), Rarg(19411), Rxrb(20182) expand Show data source
Purity
>98% expand Show data source
≥98% (HPLC) expand Show data source
≥98.0% (HPLC) expand Show data source
95+% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Impurities
≤0.002% heavy metals expand Show data source
Loss on Drying
≤0.5% loss on drying expand Show data source
Empirical Formula (Hill Notation)
C20H28O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02158725 external link
Purity: >98%
VDR-RXR heterodimer-DNA complex destabilizer.
MP Biomedicals - 02190269 external link
All Trans Isomer
Crystalline
Reported to inhibit tumor cell proliferation in cultures.
DrugBank - DB00982 external link
Item Information
Drug Groups approved
Description Isotretinoin is a medication used for the treatment of severe acne. It is sometimes used in prevention of certain skin cancers. It is a retinoid, meaning it derives from vitamin A and is found in small quantities naturally in the body. Isotretinoin binds to and activates nuclear retinoic acid receptors (RAR), thereby regulating cell proliferation and differentiation. This agent also exhibits immunomodulatory and anti-inflammatory responses and inhibits ornithine decarboxylase, thereby decreasing polyamine synthesis and keratinization.
Indication For the treatment of severe recalcitrant nodular acne
Pharmacology Isotretinoin, a retinoid, is indicated in the treatment of severe recalcitrant nodular acne. Nodules are inflammatory lesions with a diameter of 5 mm or greater. The nodules may become suppurative or hemorrhagic. "Severe," by definition, means "many" as opposed to "few or several" nodules. Clinical improvement in nodular acne patients occurs in association with a reduction in sebum secretion. The decrease in sebum secretion is temporary and is related to the dose and duration of treatment with Accutane, and reflects a reduction in sebaceous gland size and an inhibition of sebaceous gland differentiation.
Toxicity Isotretinoin is teratogenic. It also causes mucocutaneous side effects suck as cheilitis, dry skin, and dry eyes.
Affected Organisms
Humans and other mammals
Half Life 17-50 hours
Protein Binding 99.9%
Elimination Isotretinoin and its metabolites are further metabolized into conjugates, which are then excreted in urine and feces. The metabolites of isotretinoin and any conjugates are ultimately excreted in the feces and urine in relatively equal amounts (total of 65% to 83%).
Clearance * 96 +/- 6.27 L/hr [severe recalcitrant nodular acne pediatric Patients, 12 to 15 Years]
References
Berard A, Azoulay L, Koren G, Blais L, Perreault S, Oraichi D: Isotretinoin, pregnancies, abortions and birth defects: a population-based perspective. Br J Clin Pharmacol. 2007 Feb;63(2):196-205. [Pubmed]
Holmes SC, Bankowska U, Mackie RM: The prescription of isotretinoin to women: is every precaution taken? Br J Dermatol. 1998 Mar;138(3):450-5. [Pubmed]
Amichai B, Shemer A, Grunwald MH: Low-dose isotretinoin in the treatment of acne vulgaris. J Am Acad Dermatol. 2006 Apr;54(4):644-6. [Pubmed]
Seukeran DC, Cunliffe WJ: Acne vulgaris in the elderly: the response to low-dose isotretinoin. Br J Dermatol. 1998 Jul;139(1):99-101. [Pubmed]
Tirado Sanchez A, Leon Dorantes G: [Erectile dysfunction during isotretinoin therapy] Actas Urol Esp. 2005 Nov-Dec;29(10):974-6. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
DrugBank - DB00755 external link
Item Information
Drug Groups approved; nutraceutical; investigational
Description Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL).
Indication For the the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant); For the topical treatment of acne vulgaris, flat warts and other skin conditions (psoriasis, ichthyosis congenita, icthyosis vulgaris, lamellar icthyosis, keratosis palmaris et plantaris, epidermolytic hyperkeratosis, senile comedones, senile keratosis, keratosis follicularis (Darier's disease), and basal cell carcinomas.); For palliative therapy to improve fine wrinkling, mottled hyperpigmentation, roughness associated with photodamage.
Pharmacology Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL).
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption 1-31% (topical)
Half Life 0.5-2 hours
Protein Binding > 95%
References
Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, Gu LJ, Wang ZY: Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood. 1988 Aug;72(2):567-72. [Pubmed]
Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L: All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results. Blood. 1990 Nov 1;76(9):1704-9. [Pubmed]
Sanz MA: Treatment of acute promyelocytic leukemia. Hematology Am Soc Hematol Educ Program. 2006;:147-55. [Pubmed]
Mao JT, Goldin JG, Dermand J, Ibrahim G, Brown MS, Emerick A, McNitt-Gray MF, Gjertson DW, Estrada F, Tashkin DP, Roth MD: A pilot study of all-trans-retinoic acid for the treatment of human emphysema. Am J Respir Crit Care Med. 2002 Mar 1;165(5):718-23. [Pubmed]
Roth MD, Connett JE, D'Armiento JM, Foronjy RF, Friedman PJ, Goldin JG, Louis TA, Mao JT, Muindi JR, O'Connor GT, Ramsdell JW, Ries AL, Scharf SM, Schluger NW, Sciurba FC, Skeans MA, Walter RE, Wendt CH, Wise RA: Feasibility of retinoids for the treatment of emphysema study. Chest. 2006 Nov;130(5):1334-45. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1653 external link
Research Area: Cancer
Biological Activity:
Tretinoin is an agent which is commonly used to treat acne vulgaris and keratosis pilaris. Its success in treating acute promyelocytic leukemia was a major breakthrough in the treatment of this type of leukemia. It works in APL because the majority of cases involve a chromosomal translocation of chromosomes 15 and 17, which causes genetic fusion of the retinoic acid receptor (RAR) gene to the promyelocytic leukemia (PML) gene. This fusion PML-RAR protein is responsible for preventing immature myeloid cells from differentiating into more mature cells. [1]
Selleck Chemicals - S1379 external link
Research Area: Acne
Biological Activity:
Isotretinoin is a medication used for the treatment of severe acne. It was first developed to be used as a chemotherapy medication for the treatment of brain cancer, pancreatic cancer and more. It is still used in the treatment of these cancers to this day because of its ability to kill rapidly dividing cells. [1]
Sigma Aldrich - R2625 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
包装
1, 5 g in ampule
50, 100, 500 mg in ampule
Sealed ampule
Biochem/physiol Actions
all-trans-Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R2625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - R3255 external link
Biochem/physiol Actions
13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R3255.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - 95152 external link
Other Notes
Review: Retinoic acid metabolism1
Unit Definition
1 U corresponds to 1 international U acc. to Ph Eur II, 217 (1983)
Biochem/physiol Actions
all-trans-Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons.
Toronto Research Chemicals - R250200 external link
Physiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation.
Toronto Research Chemicals - R245015 external link
An endogenous retinoid that induces liver fibrosis via the activation of latent transforming growth factor-β. A major plasma metabolite of 9-cis Retinoic Acid (R245000).
Toronto Research Chemicals - R250000 external link
Used as a treatment for severe acne. Presently being studied in conjuction with the treatment of photoaged skin.
Toronto Research Chemicals - R245020 external link
A retinoid compound with reduced toxicity than the starting or parent retinoid.
Toronto Research Chemicals - R245030 external link
An impurity of Isotretinoin as per European Pharmacopoeia.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • Holmes SC, Bankowska U, Mackie RM: The prescription of isotretinoin to women: is every precaution taken? Br J Dermatol. 1998 Mar;138(3):450-5. Pubmed
  • • Amichai B, Shemer A, Grunwald MH: Low-dose isotretinoin in the treatment of acne vulgaris. J Am Acad Dermatol. 2006 Apr;54(4):644-6. Pubmed
  • • Seukeran DC, Cunliffe WJ: Acne vulgaris in the elderly: the response to low-dose isotretinoin. Br J Dermatol. 1998 Jul;139(1):99-101. Pubmed
  • • Tirado Sanchez A, Leon Dorantes G: [Erectile dysfunction during isotretinoin therapy] Actas Urol Esp. 2005 Nov-Dec;29(10):974-6. Pubmed
  • • Berard A, Azoulay L, Koren G, Blais L, Perreault S, Oraichi D: Isotretinoin, pregnancies, abortions and birth defects: a population-based perspective. Br J Clin Pharmacol. 2007 Feb;63(2):196-205. Pubmed
  • • Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, Gu LJ, Wang ZY: Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood. 1988 Aug;72(2):567-72. Pubmed
  • • Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L: All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results. Blood. 1990 Nov 1;76(9):1704-9. Pubmed
  • • Sanz MA: Treatment of acute promyelocytic leukemia. Hematology Am Soc Hematol Educ Program. 2006;:147-55. Pubmed
  • • Mao JT, Goldin JG, Dermand J, Ibrahim G, Brown MS, Emerick A, McNitt-Gray MF, Gjertson DW, Estrada F, Tashkin DP, Roth MD: A pilot study of all-trans-retinoic acid for the treatment of human emphysema. Am J Respir Crit Care Med. 2002 Mar 1;165(5):718-23. Pubmed
  • • Roth MD, Connett JE, D'Armiento JM, Foronjy RF, Friedman PJ, Goldin JG, Louis TA, Mao JT, Muindi JR, O'Connor GT, Ramsdell JW, Ries AL, Scharf SM, Schluger NW, Sciurba FC, Skeans MA, Walter RE, Wendt CH, Wise RA: Feasibility of retinoids for the treatment of emphysema study. Chest. 2006 Nov;130(5):1334-45. Pubmed
  • • http://en.wikipedia.org/wiki/Tretinoin
  • •  http://en.wikipedia.org/wiki/Isotretinoin
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