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68-22-4 molecular structure
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(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

ChemBase ID: 598
Molecular Formular: C20H26O2
Molecular Mass: 298.41924
Monoisotopic Mass: 298.19328007
SMILES and InChIs

SMILES:
O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CC(=O)CC2)CC3)CC1)C)C#C
Canonical SMILES:
C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
InChI:
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
InChIKey:
VIKNJXKGJWUCNN-XGXHKTLJSA-N

Cite this record

CBID:598 http://www.chembase.cn/molecule-598.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
IUPAC Traditional name
norethindrone
Brand Name
Anhydrohydroxynorprogesterone
Anovulatorio
Anovule
Aygestin
Binovum
Brevicon
Brevinor
Brevinor 21
Brevinor 28
Brevinor-1 21
Brevinor-1 28
Camila
Ciclovulan
Conceplan
Conludaf
Conludag
Demulen
ENT
Errin
Estrinor
Ethinylnortestosterone
Ethynylmortestosterone
Ethynylnortestosterone
Gencept
Genora
Gestest
Jenest
Jenest-28
Loestrin
Menzol
Microneth
Micronett
Micronor
Micronovum
Milli
Mini-Pe
Mini-Pill
Minovlar
Modicon
N.E.E.
NET
Necon
Nelova
Neocon
Nodiol
Nor-Q.D.
Nor-Qd
Noraethisteronum
Noralutin
Norcept
Norcept-E
Norcolut
Noresthisterone
Norethadrone
Norethin
Norethin 1/35 E
Norethin 1/50 M
Norethindrone Acetate
Norethindrone Norethisterone
Norethisteron
Norethisterone
Norethisterone [Progestins]
Norethisteronum [INN-Latin]
Norethyndron
Norethynodron
Norethynodrone
Noretisterona [INN-Spanish]
Noretisterone [Dcit]
Norfor
Norgestin
Noriday
Noriday 28
Norimin
Norinyl
Norlestrin
Norlutate
Norluten
Norlutin
Norluton
Normapause
Norpregneninlone
Norpregneninolone
Norpregneninotone
Orlest
Ortho 1 35
Ortho 7 7 7
Ortho-Novum
Ortho-Novum 1 35
Ortho-Novum 1 50
Ortho-Novum 7 7 7
Ovcon
Ovysmen
Ovysmen 0.5 35
Ovysmen 1 35
Palonyl
Perovex
Primolut N
Primolut-N
Proluteasi
Synphase
Synphasic 28
Tri-Norinyl
Triella
Trinovum
Trinovum 21
Utovlan
Utovlar
Loestrin 24 Fe
Synonyms
Norethindrone
19-Norethindrone
17α-Ethynyl-19-nortestosterone
17-Hydroxy-19-nor-17α-4-pregnen-20-yn-3-one
17α-Ethynyl-17β-hydroxy-19-nor-4-androsten-3-one
19-Nor-17α-ethynyl-4-androsten-17β-ol-3-one
19-Norethisterone
(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
17α-Ethynyl-17 β-hydroxy-19-nor-4-androsten-3-one
17α-Ethynyl-19-nortestosterone
17α-乙炔基-19-去甲睾酮
17-羟基-19-去甲-17α-孕甾-4-烯-20-炔基-3-酮
17α-乙炔基-17β-羟基-19-去甲-4-雄甾烯-3-酮
19-去甲-17α-乙炔基-4-雄甾烯-17β-醇-3-酮
去甲基脱氢羟孕酮
炔诺酮
CAS Number
68-22-4
EC Number
200-681-6
MDL Number
MFCD00067596
Beilstein Number
1915671
PubChem SID
24897669
46504816
160964061
24870259
PubChem CID
6230

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.594933  H Acceptors
H Donor LogD (pH = 5.5) 3.217228 
LogD (pH = 7.4) 3.217228  Log P 3.217228 
Molar Refractivity 87.4245 cm3 Polarizability 34.003754 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.72  LOG S -4.65 
Solubility (Water) 6.68e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
7.04 mg/L expand Show data source
chloroform: ≥50 mg/mL, clear, colorless expand Show data source
Apperance
white to off-white powder expand Show data source
Melting Point
203-204 °C expand Show data source
205-206 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -24°, c = 1 in chloroform expand Show data source
Hydrophobicity(logP)
3.2 expand Show data source
Storage Condition
protect from light expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
RC8975000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) 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
German water hazard class
3 expand Show data source
Risk Statements
40 expand Show data source
R:45 expand Show data source
Safety Statements
22-36/37/39-45 expand Show data source
S:28-36/37/39-45-53 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H351 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
human ... AR(367), PGR(5241)rat ... Ar(24208) expand Show data source
Purity
≥98% expand Show data source
98% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
vial of 250 mg expand Show data source
Empirical Formula (Hill Notation)
C20H26O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02155946 external link
(17α-Ethynyl-17β-hydroxy-19-nor-4-androsten-3-one; 17α-Ethynyl-19-nortestosterone) Crystalline
DrugBank - DB00717 external link
Item Information
Drug Groups approved
Description A synthetic progestational hormone with actions similar to those of progesterone but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception. [PubChem]
Indication For use as an oral contraceptive in the prevention of pregnancy.
Pharmacology Norethindrone is a synthetic oral progestin. It is used for contraception or to treat such conditions as secondary amenorrhea, abnormal uterine bleeding, and endometriosis. As an oral contraceptive, norethindrone is available as either a single agent or in combination with an estrogen.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Absolute oral bioavailability approximately 64%
Half Life 7 hours
Protein Binding >95%
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - N6384 external link
Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
包装
Supplied in amber screw-cap vials
Sigma Aldrich - N4128 external link
Biochem/physiol Actions
炔诺酮是用于抑制细胞溶质磺基转移酶类 (SULT) 的口服避孕药。
包装
1, 5 g in glass bottle
250 mg in glass bottle
50 mg in poly bottle
Sigma Aldrich - 286850 external link
Biochem/physiol Actions
19-norethindrone is an oral contraceptive involved in the inhibition of cytosolic sulfotransferases (SULT).
Sigma Aldrich - 46525 external link
Biochem/physiol Actions
19-norethindrone is an oral contraceptive involved in the inhibition of cytosolic sulfotransferases (SULT).
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

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PATENTS

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