Carboprost

Title: Carboprost
CAS Registry Number: 35700-23-3
CAS Name: (5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic acid
Additional Names: 7-[3,5-dihydroxy-2-(3-hydroxy-3-methyl-1-octenyl)cyclopentyl]-5-heptenoic acid; (15S)-15-methyl PGF2a
Manufacturers' Codes: U-32921
Molecular Formula: C21H36O5
Molecular Weight: 368.51
Percent Composition: C 68.44%, H 9.85%, O 21.71%
Literature References: Analog of prostaglandin F2a, q.v. Prepn: G. L. Bundy et al., DE 2121980; G. L. Bundy, US 3728382 (1971, 1973 both to Upjohn); eidem, Ann. N.Y. Acad. Sci. 180, 76 (1971); E. W. Yankee et al., J. Am. Chem. Soc. 96, 5865 (1974). Biological activity: J. R. Weeks et al., J. Pharmacol. Exp. Ther. 186, 67 (1973). Mechanism of action: A. I. Csapo, M. O. Pulkkinen, Prostaglandins 18, 479 (1979). Clinical studies: P. C. Schwallie, K. R. Lamborn, J. Reprod. Med. 23, 289 (1979); M. P. Mapa et al., Int. J. Gynaecol. Obstet. 20, 125 (1982). Teratological study: G. M. Szczech et al., Adv. Prostaglandin Thromboxane Res. 4, 157 (1978).
Derivative Type: Tromethamine salt
CAS Registry Number: 58551-69-2
Additional Names: Carboprost trometamol
Manufacturers' Codes: U-32921E
Trademarks: Hemabate (Pfizer); Prostin/15M (Pfizer)
Molecular Formula: C25H47NO8
Molecular Weight: 489.64
Percent Composition: C 61.32%, H 9.68%, N 2.86%, O 26.14%
Derivative Type: Methyl ester
CAS Registry Number: 35700-21-1
Additional Names: Carboprost methyl
Manufacturers' Codes: U-36384
Molecular Formula: C22H38O5
Molecular Weight: 382.53
Percent Composition: C 69.08%, H 10.01%, O 20.91%
Properties: Crystals from ether/hexane, mp 55-56°. [a]D +24° (c = 0.81 in ethanol).
Melting point: mp 55-56°
Optical Rotation: [a]D +24° (c = 0.81 in ethanol)
Therap-Cat: Oxytocic.
Keywords: Oxytocic; Prostaglandin/Prostaglandin Analog.
Carboquone Carbostyril Carbosulfan Carboxin Carboxymethylcellulose Sodium

Carboprost
Carboprost.svg
Systematic (IUPAC) name
(5Z,9α,11α,13E,15S)-9,11,15-trihydroxy-15- methylprosta-5,13-dien-1-oic acid
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a600042
Pregnancy cat. c
Legal status Prescription only
Routes Intravenous
Identifiers
CAS number 58551-69-2 YesY
ATC code G02AD04
PubChem CID 5281075
DrugBank DB00429
ChemSpider 4444532 YesY
UNII U4526F86FJ YesY
ChEMBL CHEMBL1201299 N
Chemical data
Formula C21H36O5 
Mol. mass 368.508 g/mol
 N (what is this?)  (verify)

Carboprost (INN, trade names for the tromethamine salts Hemabate, Tham) is a synthetic prostaglandin analogue of PGF (specifically, it is 15-methyl-PGF) with oxytocic properties.

Carboprost induces contractions and can trigger abortion in early pregnancy. It also reduces postpartum bleeding.