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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H40O6
Molecular Weight 460.6029
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROCORTISONE CAPROATE

SMILES

[H][C@@]12CC[C@](O)(C(=O)COC(=O)CCCCC)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=XZSVYVIYKBHVMV-FOMYWIRZSA-N
InChI=1S/C27H40O6/c1-4-5-6-7-23(31)33-16-22(30)27(32)13-11-20-19-9-8-17-14-18(28)10-12-25(17,2)24(19)21(29)15-26(20,27)3/h14,19-21,24,29,32H,4-13,15-16H2,1-3H3/t19-,20-,21-,24+,25-,26-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H40O6
Molecular Weight 460.6029
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Hydrocortisone caproate is a synthetic steroid hormone and 21-O-hexanoyl derivative of hydrocortisone. Hydroxyprogesterone caproate was previously marketed under the trade name Delalutin by Squibb, which was approved by the U.S. Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999. Hydrocortisone caproate acts by binding to progesterone receptors in the uterus, ovaries, breasts and in the central nervous system. These receptors exist in 2 isoforms, PR-A and PR-B. Hydrocortisone caproate binding to these receptors ultimately leads to regulation of gene transcription. This results in an anti-inflammatory effect which blunts the proinflammatory state that occurs with the initiation of labor and maintains uterine quiescence by stabilizing progesterone acting on the myometrium. Following intramuscular injection, approximately 50% of hydroxyprogesterone caproate metabolites are eliminated in the feces, while approximately 30% of metabolites are eliminated in the urine. Injection site pain is the most common adverse effect associated with hydroxyprogesterone caproate. Other commonly reported adverse effects include injection site swelling, urticaria, pruritus, injection site pruritus, nausea, injection site nodule, and diarrhea.

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 05:50:52 GMT 2023
Edited
by admin
on Sat Dec 16 05:50:52 GMT 2023
Record UNII
SAE475O6E4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROCORTISONE CAPROATE
JAN   WHO-DD  
Common Name English
Hydrocortisone caproate [WHO-DD]
Common Name English
HEXANOIC ACID, 21-ESTER WITH CORTISOL
Common Name English
CORTISOL, 21-HEXANOATE
Common Name English
HYDROCORTISONE 21-HEXANOATE
Common Name English
PREGN-4-ENE-3,20-DIONE, 11,17-DIHYDROXY-21-((1-OXOHEXYL)OXY)-, (11.BETA.)-
Systematic Name English
HYDROCORTISONE 21-CAPROATE
Common Name English
HYDROCORTISONE CAPROATE [JAN]
Common Name English
HYDROCORTISONE HEXANOATE
Common Name English
Code System Code Type Description
PUBCHEM
107423
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID20872908
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
SMS_ID
100000153082
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
EVMPD
SUB126894
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
CHEBI
31676
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-737-9
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
CAS
3593-96-2
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY
FDA UNII
SAE475O6E4
Created by admin on Sat Dec 16 05:50:52 GMT 2023 , Edited by admin on Sat Dec 16 05:50:52 GMT 2023
PRIMARY