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Carboprost

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Revision as of 20:11, 10 November 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Carboprost
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa600042
Pregnancy
category
  • c
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (5Z,9α,11α,13E,15S)-9,11,15-trihydroxy-15- methylprosta-5,13-dien-1-oic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H36O5
Molar mass368.508 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C(O)CCC/C=C/C1(O)C(O)1/C=C/(O)(C)CCCCC
InChI
  • InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
  • Key:DLJKPYFALUEJCK-IIELGFQLSA-N
  (what is this?)  (verify)

Carboprost (INN, trade names for the tromethamine salts Hemabate, Tham) is a synthetic prostaglandin analogue of PGF2α (specifically, it is 15-methyl-PGF2α) with oxytocic properties.

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

Indication

Used in postpartum hemorrhage caused by uterine atony not controlled by other methods.
Unlabeled use:

  • Hemorrhagic Cystitis
  • PID

Contraindication

Contraindicated in severe cardiovascular, renal, and hepatic disease, also contraindicated in Pelvic Inflammatory Disease. Exert caution in asthmatic patients.

Precautions

  • asthma
  • anemia
  • jaundice
  • diabetes mellitus
  • seizure disorders
  • past uterine surgery

Adverse Effects

  • diarrhea (most common, may be sudden in onset)
  • fever
  • chills
  • nausea/vomiting

References

External links

  • Carboprost at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  • Indman P (2004). "Use of carboprost to facilitate hysteroscopic resection of submucous myomas". J Am Assoc Gynecol Laparosc. 11 (1): 68–72. doi:10.1016/S1074-3804(05)60014-X. PMID 15104835.
  • Vukelić J (2001). "Second trimester pregnancy termination in primigravidas by double application of dinoprostone gel and intramuscular administration of carboprost tromethamine". Med Pregl. 54 (1–2): 11–6. PMID 11436877.
  • Ippoliti C, Przepiorka D, Mehra R, Neumann J, Wood J, Claxton D, Gajewski J, Khouri I, van Besien K, Andersson B (1995). "Intravesicular carboprost for the treatment of hemorrhagic cystitis after marrow transplantation". Urology. 46 (6): 811–5. doi:10.1016/S0090-4295(99)80349-5. PMID 7502421.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Eicosanoids
Precursor
Prostanoids
Prostaglandins (PG)
Precursor
Active
D/J
E/F
I
Thromboxanes (TX)
Leukotrienes (LT)
Precursor
Initial
SRS-A
Eoxins (EX)
Precursor
Eoxins
Nonclassic
By function
Uterotonics/labor inducers/oxytocics (G02A)
Cervical ripening
Ergot alkaloids
Prostaglandins and
analogues
Contraction induction


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