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520-85-4 molecular structure
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(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

ChemBase ID: 485
Molecular Formular: C22H32O3
Molecular Mass: 344.48768
Monoisotopic Mass: 344.23514488
SMILES and InChIs

SMILES:
O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)[C@H](C3)C)C)CC2)CC1)C)C(=O)C
Canonical SMILES:
O=C1CC[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
InChI:
InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
InChIKey:
FRQMUZJSZHZSGN-HBNHAYAOSA-N

Cite this record

CBID:485 http://www.chembase.cn/molecule-485.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
IUPAC Traditional name
medroxyprogesterone
Brand Name
Aragest
Aragest 5
Asconale
Clinofem
Clinovir
Colirest
DMPA
Depo-Clinovir
Depo-Prodasone
Depo-Progestin
Depo-Promone
Depot-Medroxyprogesterone acetate
Farlutal
Farlutin
G-Farlutal
Gestapuran
Hematrol
Hysron
Indivina
Lunelle
Lutopolar
Lutoral
Med-Pro
Meprate
Metigestrona
MPA Gyn 5
Nadigest
Nidaxin
Novo-Medrone
Oragest
Perlutex
Perlutex Leo
Prodasone
Progestalfa
Progevera
Proverone
Ralovera
Repromap
Repromix
Sirprogen
Sodelut G
Veramix
Provera
Synonyms
Medroxyprogesteronum [INN-Latin]
Medroxyprogesteron acetate
Medroxyprogesteron
Medroxiprogesteronum
Medroxiprogesterona [INN-Spanish]
Medrossiprogesterone [Dcit]
Medroprogesterone Acetate
MAP
Hydroxymethylprogesterone
CBP-1011
Medroxyprogesterone
6α-17-Hydroxy-6-(methyl-d3)-pregn-4-ene-3,20-dione
17α-Hydroxy-6α-methyl-progesterone
17-Hydroxy-6α-methylpregn-4-ene-3,20-dione
NSC 27408
Medroxy Progesterone
17α-Hydroxy-6α-methyl-4-pregnene-3,20-dione
17α-Hydroxy-6α-methylprogesterone
6α-Methyl-5-pregnen-17α-ol-3,20-dione
6-Dihydromegestrol
Medroxyprogesterone
17α-羟基-6α-甲基-4-孕烯-3,20-二酮
17α-羟基-6α-甲基孕酮
6α-甲基-5-孕甾烯-17α-醇-3,20-二酮
6-二氢甲地孕酮
甲羟孕酮
CAS Number
520-85-4
EC Number
208-298-6
MDL Number
MFCD00069474
Beilstein Number
2510965
PubChem SID
24870138
24897065
46508895
160963948
PubChem CID
1063110631
10631
Chemspider ID
10185
Wikipedia Title
Medroxyprogesterone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.699646  H Acceptors
H Donor LogD (pH = 5.5) 3.6881983 
LogD (pH = 7.4) 3.6881962  Log P 3.6881983 
Molar Refractivity 98.6539 cm3 Polarizability 38.85521 Å3
Polar Surface Area 54.37 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.52  LOG S -4.35 
Solubility (Water) 1.54e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
22.2mg/L expand Show data source
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Apperance
White Solid expand Show data source
Melting Point
204-206°C expand Show data source
Hydrophobicity(logP)
3.5 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
TU5300000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63-48-68 expand Show data source
Safety Statements
22-24/25 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H361 expand Show data source
GHS Precautionary statements
P281 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
Gene Information
rat ... Ar(24208) expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C22H32O3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00603 external link
Item Information
Drug Groups approved; investigational
Description (6 alpha)-17-Hydroxy-6-methylpregn-4-ene-3,20-dione. A synthetic progestational hormone used in veterinary practice as an estrus regulator. [PubChem]
Indication Used as a contraceptive and to treat secondary amenorrhea, abnormal uterine bleeding, pain associated with endometriosis, endometrial and renal cell carcinomas, paraphilia in males, GnRH-dependent forms of precocious puberty, as well as to prevent endometrial changes associated with estrogens.
Pharmacology Medroxyprogesterone is a synthetic progestin more potent than progesterone.
Toxicity Side effects include loss of bone mineral density, BMD changes in adult women, bleeding irregularities, cancer risks, and thromboembolic disorders.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Rapidly absorbed from GI tract
Half Life 50 days
Protein Binding 90%
Elimination Following oral dosing, MPA is extensively metabolized in the liver via hydroxylation, with subsequent conjugation and elimination in the urine. Most MPA metabolites are excreted in the urine as glucuronide conjugates with only minor amounts excreted as sulfates.
Clearance * 64110 +/- 42662 mL/min [postmenopausal women under fasting conditions with a single Dose of 2 × 10 mg]
* 74123 +/- 35126 mL/min [postmenopausal women under fasting conditions with a single Dose of 8 × 2.5 mg]
* 41963 +/- 38402 mL/min [postmenopausal women following daily administration of one PROVERA 10 mg tablet for 7 days]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - M6013 external link
Caution
Much of the pharmacology literature refers to medroxyprogesterone acetate as medroxyprogesterone, but they are of course not the same substance.
Sigma Aldrich - 46411 external link
Caution
Much of the pharmacology literature refers to medroxyprogesterone acetate as medroxyprogesterone, but they are of course not the same substance.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - M203550 external link
An orally active progestogen used in hormone replacement therepy (HRT), in the past has been used as a component of oral contraceptives.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Pan, Q., et al.: Mol. Hum. Reprod., 13, 797 (2007)
  • • Matsson, P., et al.: J. Pharmacol. Exp. Ther., 323, 19 (2007)
  • • Jukosky, J.A., et al.: Bull. Environ. Contam. Toxicol., 81, 230 (2007)
  • • Cherkasov, A., et al.: J. Med. Chem., 51, 2047 (2007)
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PATENTS

PATENTS

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INTERNET

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