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DSSTox_CID_28997

DSSTox_CID_28997

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Also known as: Unoprostone isopropyl ester, Unoprostone isopropyl, Rescula, 120373-24-2, Uf-021, Uf 021

Molecular Formula

C₂₅H₄₄O₅

Molecular Weight

424.6 g/mol

InChI Key

XXUPXHKCPIKWLR-JHUOEJJVSA-N

FDA UNII

5M161S5O5P

Unoprostone Isopropyl is a docosanoid and a structural analogue of an inactive biosynthetic cyclic derivative of arachidonic acid, 13,14-dihydro-15-keto-prostaglandin F 2a. Although the mechanism of action is unknown, unoprostone isopropyl may reduce elevated intraocular pressure by increasing the outflow of aqueous humor upon ocular administration.

1 2D Structure

DSSTox_CID_28997

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate

2.1.2 InChI

InChI=1S/C25H44O5/c1-4-5-6-7-10-13-20(26)16-17-22-21(23(27)18-24(22)28)14-11-8-9-12-15-25(29)30-19(2)3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21-,22-,23+,24-/m1/s1

2.1.3 InChI Key

XXUPXHKCPIKWLR-JHUOEJJVSA-N

2.1.4 Canonical SMILES

CCCCCCCC(=O)CCC1C(CC(C1CC=CCCCC(=O)OC(C)C)O)O

2.1.5 Isomeric SMILES

CCCCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)OC(C)C)O)O

2.2 Other Identifiers

2.2.1 UNII

5M161S5O5P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Eescula

2. Isopropyl 20-ethyl-9alpha,11alpha-dihydroxy-15-keto-cis-delta-5-prostanoate

3. Isopropyl Z-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate, D-

4. Rescula

5. Uf 021

6. Uf-021

7. Unoprostone Isopropyl

2.3.2 Depositor-Supplied Synonyms

1. Unoprostone Isopropyl Ester

2. Unoprostone Isopropyl

3. Rescula

4. 120373-24-2

5. Uf-021

6. Uf 021

7. Chebi:31731

8. 5m161s5o5p

9. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate

10. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate

11. Isopropyl Unoprostone (jan)

12. Isopropyl Unoprostone [jan]

13. Isopropyl (5z,9alpha,11alpha)-9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5-en-1-oate

14. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate

15. 13,14-dihydro-15-keto-20-ethyl-pgf2

16. Ocuseva

17. Unii-5m161s5o5p

18. Ncgc00183877-01

19. Dsstox_cid_28997

20. Dsstox_rid_83262

21. Dsstox_gsid_49071

22. Rescula (proposed Trade Name)

23. Schembl192726

24. Gtpl8282

25. Chembl1200661

26. Dtxsid5049071

27. Hms3648f04

28. Uf021

29. Ex-a4108

30. Tox21_113629

31. Unoprostone Isopropyl [vandf]

32. Zinc14234780

33. Unoprostone Isopropyl [mart.]

34. Akos015965062

35. Unoprostone Isopropyl [who-dd]

36. Unoprostone Isopropyl Ester [mi]

37. Unoprostone Isopropyl [orange Book]

38. Hy-109545

39. Cas-120373-24-2

40. Cs-0031289

41. D01452

42. 373u242

43. A804495

44. Sr-01000946493

45. Sr-01000946493-1

46. Q27089094

47. Isopropyl(z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-{3-oxo-1-decyl}cyclopentyl]-hept-5-enoate

48. (e)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic Acid Propan-2-yl Ester

49. 5-heptenoic Acid, 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-, 1-methylethyl Ester, (5z)-

50. Isopropyl Z-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate, (+)-

51. Isopropyl Z-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate, D-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₄₄O₅
Molecular Weight	424.6 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	17
Exact Mass	424.31887450 g/mol
Monoisotopic Mass	424.31887450 g/mol
Topological Polar Surface Area	83.8 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	514
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 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Rescula
PubMed Health	Unoprostone (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Rescula (unoprostone isopropyl ophthalmic solution) 0.15% is a synthetic docosanoid. Unoprostone isopropyl has the chemical name isopropyl (+)-(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoate. Its molecular formula is C25H44...
Active Ingredient	Unoprostone isopropyl
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.15%
Market Status	Prescription
Company	Sucampo Pharms

2 of 2
Drug Name	Rescula
PubMed Health	Unoprostone (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	Rescula (unoprostone isopropyl ophthalmic solution) 0.15% is a synthetic docosanoid. Unoprostone isopropyl has the chemical name isopropyl (+)-(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoate. Its molecular formula is C25H44...
Active Ingredient	Unoprostone isopropyl
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.15%
Market Status	Prescription
Company	Sucampo Pharms

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)