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Enprostil

Enprostil

Synopsis, Chemistry

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Also known as: 73121-56-9, Camleed, Gardrin, Rs-84135, Rs 84135-004, Gardrine

Molecular Formula

C₂₃H₂₈O₆

Molecular Weight

400.5 g/mol

InChI Key

PTOJVMZPWPAXER-VFJVYMGBSA-N

A synthetic PGE2 analog that has an inhibitory effect on gastric acid secretion, a mucoprotective effect, and a postprandial lowering effect on gastrin. It has been shown to be efficient and safe in the treatment of gastroduodenal ulcers.

1 2D Structure

Enprostil

2 Identification

2.1 Computed Descriptors

2.1.1 InChI

InChI=1S/C23H28O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-20,22,24,26H,8,11-12,15-16H2,1H3/b14-13+/t2?,17-,19-,20-,22-/m1/s1

2.1.2 InChI Key

PTOJVMZPWPAXER-VFJVYMGBSA-N

2.1.3 Canonical SMILES

COC(=O)CCC=C=CCC1C(C(CC1=O)O)C=CC(COC2=CC=CC=C2)O

2.1.4 Isomeric SMILES

COC(=O)CCC=C=CC[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/[C@H](COC2=CC=CC=C2)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Enprostil, (1alpha(r*),2beta(1e,3r*),3alpha)-(+-)-isomer

2. Enprostil, (1alpha(r*),2beta(1e,3s*),3alpha)-(+-)-isomer

3. Enprostil, (1alpha,2alpha(1e,3s*),3beta)-(+-)-isomer

4. Enprostil, (1alpha,2beta(1e,3r*),3alpha)-(+-)-isomer

5. Enprostil, (1r-(1(r*),2beta(1e,3r*),3alpha))-isomer

6. Enprostil, (1r-(1alpha(s*),2beta(1e,3r*),3alpha))-isomer

7. Enprostil, (1r-(1alpha,2beta(1e,3r*),3alpha))-isomer

8. Enprostil, (1s-(1alpha(r*),2beta(1e,3r*),3alpha))-isomer

9. Enprostil, (1s-(1alpha(s*),2beta(1e,3r*),3alpha))-isomer

10. Gardrin

11. Rs 84135

12. Rs-84135

13. Rs84135

2.2.2 Depositor-Supplied Synonyms

1. 73121-56-9

2. Camleed

3. Gardrin

4. Rs-84135

5. Rs 84135-004

6. Gardrine

7. Syngard

8. Enprostil (jan/usan/inn)

9. Camleed (tn)

10. Rs-86505-007

11. Schembl186877

12. Gtpl1918

13. Chembl2104194

14. Dtxsid401021647

15. Ex-a6212

16. Zinc3812898

17. Akos016014109

18. D01891

19. Methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(e,3r)-3-hydroxy-4-(phenoxy)but-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate

2.3 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₈O₆
Molecular Weight	400.5 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	11
Exact Mass	400.18858861 g/mol
Monoisotopic Mass	400.18858861 g/mol
Topological Polar Surface Area	93.1 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	613
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

4.2 ATC Code

A - Alimentary tract and metabolism

A02 - Drugs for acid related disorders

A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

A02BB - Prostaglandins

A02BB02 - Enprostil