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Unoprostone

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Unoprostone

Unoprostone

  • Molecular FormulaC22H38O5
  • Average mass382.534 Da
[1R-[1a(Z),2b,3a,5a]]-7-[3,5-Dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic acid
120373-36-6 [RN]
13,14-Dihydro-15-keto-20-ethyl-PGF2a
6920
6X4F561V3W
CAS Registry Number: 120373-36-6
CAS Name: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic acid
Additional Names: 13,14-dihydro-15-keto-20-ethyl-PGF2a
Molecular Formula: C22H38O5
Molecular Weight: 382.53
Percent Composition: C 69.08%, H 10.01%, O 20.91%
Literature References: Prepn: R. Ueno et al., EP 289349eidem, US 5221763 (1988, 1993 both to Ueno). Pharmacological characterization: Y. Goh, J. Kishino, Jpn. J. Ophthalmol. 38, 236 (1994). Mechanism of action study: M. Sakurai et al., ibid. 37, 252 (1993). Comparative clinical trial in glaucoma and ocular hypertension: J.-P. Nordmann et al., Am. J. Ophthalmol. 133, 1 (2002).
2D chemical structure of 120373-24-2
13,14-Dihydro-15-keto-20-ethyl-PGF2
Derivative Type: Isopropyl ester
CAS Registry Number: 120373-24-2
Manufacturers’ Codes: UF-021
Trademarks: Rescula (Novartis)
Molecular Formula: C25H44O5
Molecular Weight: 424.61
Percent Composition: C 70.72%, H 10.44%, O 18.84%
Therap-Cat: Antiglaucoma; in treatment of ocular hypertension.
Keywords: Antiglaucoma; Prostaglandin/Prostaglandin Analog.

Unoprostone (INN) is a prostaglandin analogue. Its isopropyl esterunoprostone isopropyl, was marketed under the trade name Rescula for the management of open-angle glaucoma and ocular hypertension, but is now discontinued in the US.[1]

Unoprostone isopropyl is a prostaglandin analogue. 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. The main indication of Unoprostane is treatment of glucoma.

This compound can be prepared by two different ways: 1) The reaction of 1-benzyl-4-(hydroxymethyl)pyrrolidin-2-one (I) with SOCl2 in refluxing dichloromethane gives 1-benzyl-4-(chloromethyl)pyrrolidin-2-one (II), which is condensed with potassium phthalimide (III) in DMF yielding 1-benzyl-4-(phthalimidomethyl)pyrrolidin-2-one (IV). Finally, this compound is treated with hydrazine in ethanol and neutralized with fumaric acid. 2) The dehydration of 1-benzyl-2-oxo-pyrrolidine-4-carboxamide (V) with POCl3 in hot DMF gives 1-benzyl-4-cyanopyrrolidine-2-one (VI), which is reduced with H2 and RaNi in methanol – NH3 and neutralized with fumaric acid. EP 0289349; JP 1989151552; US 5001153; US 5106869

syn 2

The condensation of dimethyl methylphosphonate (I) with ethyl octanoate (II) by means of butyllithium in THF gives dimethyl 2-oxononylphosphonate (III), which is condensed with the protected aldehyde (IV) by means of NaH in THF, yielding the unsaturated ketone (V). The hydrogenation of (V) with H2 over Pd/C in ethyl acetate affords the corresponding saturated ketone (VI), which is treated with ethylene glycol and p-toluenesulfonic acid to give the cyclic ketal (VII). The mild hydrolysis of (VII) with K2CO3 and acetic acid gives the alcohol derivative (VIII); the reduction of the lactone group of (VIII) with dibutylaluminum hydride in toluene affords the lactol (IX), which is condensed with (4-carboxybutyl)triphenylphosphonium bromide (X) by means of NaH in DMSO yielding the protected prostaglandin (XI). Esterification of (XI) with isopropyl iodide and DBU in acetonitrile gives the precursor (XII), which is finally deprotected with acetic acid in THF – water.

References

Unoprostone
Unoprostone.svg
Clinical data
Trade names Rescula
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Topical (eye drops)
ATC code
Legal status
Legal status
  • US: Discontinued
Pharmacokinetic data
Elimination half-life 14 min
Excretion Renal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.227.145 Edit this at Wikidata
Chemical and physical data
Formula C22H38O5
Molar mass 382.534 g/mol g·mol−1
3D model (JSmol)

///////////////Antiglaucoma, ocular hypertension, UF-021, Unoprostone

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

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


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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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