U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32O4
Molecular Weight 372.4978
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORGESTOMET

SMILES

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)C[C@H](C)[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=IWSXBCZCPVUWHT-VIFKTUCRSA-N
InChI=1S/C23H32O4/c1-13-12-22(4)20(9-10-23(22,14(2)24)27-15(3)25)19-7-5-16-11-17(26)6-8-18(16)21(13)19/h11,13,18-21H,5-10,12H2,1-4H3/t13-,18-,19-,20-,21+,22-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H32O4
Molecular Weight 372.4978
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Norgestomet is a synthetic derivative of progesterone with improved oral activity due to its 17α-acetate side chain. In veterinary medicine norgestomet is used for the synchronisation of oestrus in cattle. It is administered as a subcutaneous ear implant (containing 3 mg norgestomet; to be removed after 9 to 10 days), in combination with a single intramuscular injection containing 3 mg norgestomet and 5 mg oestradiol valerate. The injection is to be given immediately after application of the implant. Norgestomet is not used in human medicine. It is a steroidal progestin of the 19-norprogesterone group.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.44 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Norgestomet

Approved Use

In veterinary medicine norgestomet is used for the synchronisation of oestrus in cattle.

Launch Date

2004
PubMed

PubMed

TitleDatePubMed
Controlled drug release from polymeric delivery devices IV: in vitro--in vivo correlation of subcutaneous release of norgestomet from hydrophilic implants.
1976 Apr
Mechanisms regulating norgestomet inhibition of endometrial gland morphogenesis in the neonatal ovine uterus.
2000 Sep
Patents

Sample Use Guides

Cattle: It is administered as a subcutaneous ear implant (containing 3 mg norgestomet; to be removed after 9 to 10 days), in combination with a single intramuscular injection containing 3 mg norgestomet and 5 mg oestradiol valerate. The injection is to be given immediately after application of the implant.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: A bioassay based on the stimulation of estrogen-dependent proliferation of human breast cancer-derived MCF-7 cells was used.
Estimated values at which 50% of the specific binding of 16 nM [3H]progesterone was competitively inhibited separately by unlabeled norgestomet or progesterone, were 2.44 nM and 17.7 nM, respectively. Half-maximal stimulation of response by norgestomet was approximately 50 uM, although stimulation never exceeded 50% any of the concentrations used, and the relative estrogenic activity of norgestomet was 20 million-fold weaker than the activity of 17b-estradiol. Estrogenic activity was observed only above 1 uM (about 0.3 ug/ml). Addition of norgestomet (10 uM) to culture media increased (p<.01) estrogenic activity
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:51:45 GMT 2023
Edited
by admin
on Sat Dec 16 17:51:45 GMT 2023
Record UNII
3L33UD42X4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORGESTOMET
GREEN BOOK   INN   MART.   USAN  
INN   USAN  
Official Name English
NORGESTOMET [MART.]
Common Name English
NORGESTOMET [GREEN BOOK]
Common Name English
NORGESTOMET [USAN]
Common Name English
17-Hydroxy-11β-methyl-19-norpregn-4-ene-3,20-dione acetate
Common Name English
norgestomet [INN]
Common Name English
19-NORPREGN-4-ENE-3,20-DIONE, 17-(ACETYLOXY)-11-METHYL-, (11.BETA.)-
Common Name English
SC-21009
Code English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
CFR 21 CFR 522.850
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
246-611-8
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID901016491
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
DRUG BANK
DB11440
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
INN
3663
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
WIKIPEDIA
Norgestomet
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
CAS
25092-41-5
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
SMS_ID
100000083598
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104744
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
PUBCHEM
9820838
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
EVMPD
SUB09370MIG
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
NCI_THESAURUS
C77015
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
FDA UNII
3L33UD42X4
Created by admin on Sat Dec 16 17:51:45 GMT 2023 , Edited by admin on Sat Dec 16 17:51:45 GMT 2023
PRIMARY
Related Record Type Details
TARGET->ANALOGUE
Related Record Type Details
ACTIVE MOIETY