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Chemistry

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Also known as: Hemabate, 58551-69-2, Carboprost trometamol, Prostinfenem, Carboprost trometanol, Carboprost (tromethamine)
Molecular Formula
C25H47NO8
Molecular Weight
489.6  g/mol
InChI Key
UMMADZJLZAPZAW-XOWPVRJPSA-N
FDA UNII
U4526F86FJ

Carboprost Tromethamine
Carboprost Tromethamine is the tromethamine salt of the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 alpha (PGF2 alpha) with oxytocic activity. Mimicking endogenous PGF2 alpha, carboprost activates prostaglandin F receptor, a G-protein coupled receptor, on smooth muscle cells, thereby resulting in smooth muscle contractions. When administered intramuscularly on gravid subjects, this agent induces myometrium contractions, thereby initiating luteolysis and consequently parturition. Furthermore, carboprost's action on vascular smooth muscle and gastrointestinal tract sphincters leads to raised blood pressure and induces vomiting or diarrhea, respectively.
1 2D Structure

Carboprost Tromethamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-amino-2-(hydroxymethyl)propane-1,3-diol;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid
2.1.2 InChI
InChI=1S/C21H36O5.C4H11NO3/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;5-4(1-6,2-7)3-8/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25);6-8H,1-3,5H2/b7-5-,14-12+;/t16-,17-,18+,19-,21+;/m1./s1
2.1.3 InChI Key
UMMADZJLZAPZAW-XOWPVRJPSA-N
2.1.4 Canonical SMILES
CCCCCC(C)(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O.C(C(CO)(CO)N)O
2.1.5 Isomeric SMILES
CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O.C(C(CO)(CO)N)O
2.2 Other Identifiers
2.2.1 UNII
U4526F86FJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 15-methylprostaglandin F2alpha-tromethamine

2. Carboprost Trometamol

3. Hemabate

4. Prostin M-15

2.3.2 Depositor-Supplied Synonyms

1. Hemabate

2. 58551-69-2

3. Carboprost Trometamol

4. Prostinfenem

5. Carboprost Trometanol

6. Carboprost (tromethamine)

7. U-32921e

8. U-32,921e

9. U4526f86fj

10. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((e)-(3s)-3-hydroxy-3-methyl-1-octenyl)cyclopentyl)-5-heptenoic Acid Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

11. 2-amino-2-(hydroxymethyl)propane-1,3-diol;(z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3s)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic Acid

12. 15-methyl Prostaglandin F2alpha

13. Prostin / 15m

14. Unii-u4526f86fj

15. Carboprost Tromethamine [usan]

16. Hemabate (tn)

17. Prostin/15

18. Carboprost Tromethamine [usan:usp]

19. U 32921e

20. Carboprost Tromethanimine

21. 15-methyl Pgf2 Alpha

22. Prostin/15m

23. 15(s)15-methyl Pgf2-alpha Tromethamine Salt

24. Carboprost Tromethamine Salt

25. Schembl433085

26. 15(s)15-methyl Prostaglandin F2-alpha Tromethamine

27. Carboprost Tromethamine (usp)

28. Chembl1237105

29. (15s)-15-methylprostaglandin F(sub 2alpha) Tromethamine

30. Dtxsid601015618

31. Hy-a0195

32. Carboprost Trometamol [mart.]

33. Akos037435222

34. Carboprost Trometamol [who-dd]

35. Carboprost Tromethamine [usp-rs]

36. Carboprost Tromethamine Salt [mi]

37. Carboprost Trometamol [ep Monograph]

38. Carboprost Tromethamine [orange Book]

39. Cs-0017541

40. Carboprost Tromethamine [usp Monograph]

41. D00682

42. E78557

43. U32921

44. 551c692

45. J-507750

46. Q18578732

47. (15s)-15-methylprostaglandin F(sub 2.alpha.) Tromethamine

48. (5z,9?,11?,15e,15s)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-oic Acid Tris(hydroxymethyl)aminomethane Salt

49. 2-amino-2-(hydroxymethyl)propane-1,3-diol (e)-7-((1s,3s,5r)-3,5-dihydroxy-2-((s,z)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept- 5-enoate

50. 2-amino-2-(hydroxymethyl)propane-1,3-diol (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept-5-enoate

51. Prosta-5,13-dien-1-oic Acid, 9,11,15-trihydroxy-15-methyl-, (5z,9-alpha,11-alpha,13e,15s)-, Compd. With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

52. Prosta-5,13-dien-1-oic Acid, 9,11,15-trihydroxy-15-methyl-, (5z,9.alpha.,11.alpha.,13e,15s)-, Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 489.6 g/mol
Molecular Formula C25H47NO8
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count9
Rotatable Bond Count15
Exact Mass489.33016746 g/mol
Monoisotopic Mass489.33016746 g/mol
Topological Polar Surface Area185 Ų
Heavy Atom Count34
Formal Charge0
Complexity527
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameHemabate
PubMed HealthCarboprost Tromethamine (Injection)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelHEMABATE Sterile Solution, an oxytocic, contains the tromethamine salt of the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 in a solution suitable for intramuscular injection.Carboprost tromethamine is the established name for th...
Active IngredientCarboprost tromethamine
Dosage FormInjectable
RouteInjection
Strengtheq 0.25mg base/ml
Market StatusPrescription
CompanyPharmacia And Upjohn

2 of 2  
Drug NameHemabate
PubMed HealthCarboprost Tromethamine (Injection)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelHEMABATE Sterile Solution, an oxytocic, contains the tromethamine salt of the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 in a solution suitable for intramuscular injection.Carboprost tromethamine is the established name for th...
Active IngredientCarboprost tromethamine
Dosage FormInjectable
RouteInjection
Strengtheq 0.25mg base/ml
Market StatusPrescription
CompanyPharmacia And Upjohn

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Oxytocics

Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157) (See all compounds classified as Oxytocics.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Prostaglandins [CS]; Prostaglandin Analog [EPC]

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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,","city":"TURKAPALLY-V SHAMIRPET HYDERABAD,TE","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.03","actualQuantity":"0.00003","unit":"KGS","unitRateFc":"26100000","totalValueFC":"847.8","currency":"USD","unitRateINR":"2131474667","date":"30-Dec-2021","totalValueINR":"63944.24","totalValueInUsd":"847.8","indian_port":"HYDERABAD AIR","hs_no":"29375000","bill_no":"6894792","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON DULLES I","supplierAddress":"","customerAddress":"P.NO. 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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q1","strtotime":1674498600,"product":"CARBOPROST TROMETHAMINE USP","address":"HETERO CORPORATE, NO. 7-2-A2, INDUSTRIAL ESTATE,SANATHNAGAR Conta","city":"HYDERABAD","supplier":"CHIROGATE INTERNATIONAL","supplierCountry":"TAIWAN","foreign_port":"NA","customer":"HETERO DRUGS","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"GMS","unitRateFc":"3000","totalValueFC":"7315.5","currency":"USD","unitRateINR":"299057.6","date":"24-Jan-2023","totalValueINR":"598115.25","totalValueInUsd":"7315.5","indian_port":"HYDERABAD AIR","hs_no":"29375000","bill_no":"4339573","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"HETERO CORPORATE, NO. 7-2-A2, INDUSTRIAL ESTATE,SANATHNAGAR Conta"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1705516200,"product":"CARBOPROST TROMETHAMINE USP (FOC)","address":"6-3-865\/1\/2, FLAT NO.201,","city":"HYDERABAD, ANDHRA PRADESH","supplier":"M\/S.PFIZER, INC.","supplierCountry":"UNITED STATES","foreign_port":"NEW YORK","customer":"GLAND PHARMA LTD","customerCountry":"INDIA","quantity":"15.00","actualQuantity":"15","unit":"GMS","unitRateFc":"1626.1","totalValueFC":"24724.8","currency":"USD","unitRateINR":"136994.7","date":"18-Jan-2024","totalValueINR":"2054920.69","totalValueInUsd":"24724.8","indian_port":"Hyderabad Air","hs_no":"29335990","bill_no":"9723263","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"NEW YORK","supplierAddress":"7000 PORTAGE ROAD, KALAMAZOO,MI,SDNF UNITED STATES","customerAddress":"6-3-865\/1\/2, FLAT NO.201,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723228200,"product":"(FOC) - CARBOPROST TROMETHAMINE - H-005-384","address":"REGD. OFFICE: NO. 16\/2,","city":"BANGALORE, KARNATAKA","supplier":"CHIROGATE INTERNATIONAL","supplierCountry":"TAIWAN","foreign_port":"TAIPEI","customer":"SOMERSET THERAPEUTICS LIMITED","customerCountry":"INDIA","quantity":"70.00","actualQuantity":"70","unit":"GMS","unitRateFc":"2500","totalValueFC":"178631","currency":"USD","unitRateINR":"214047.3","date":"10-Aug-2024","totalValueINR":"14983307.82","totalValueInUsd":"178631","indian_port":"Bangalore Air","hs_no":"29379090","bill_no":"4990360","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"TAIPEI","supplierAddress":"NO 2 SHIH 4TH RD YANGMEI DIST TAOYUAN CITY 326013 TAIWAN Taipei, , Taiwan Taiwan","customerAddress":"REGD. OFFICE: NO. 16\/2,"}]
06-Mar-2021
12-Aug-2024
GMS
overview
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Average Price (USD/GMS)

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Quantity (GMS) & Unit rate (USD/GMS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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