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Alatrofloxacin Mesylate

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Alatrofloxacin Mesylate

Chemical Names: Alatrofloxacin mesylate; UNII-2IXX802851; 146961-77-5; Alatrofloxacin mesylate [USAN]; 157605-25-9; 2IXX802851
Molecular Formula: C27H29F3N6O8S
Molecular Weight: 654.618 g/mol
CAS No. 146961-76-4 (Alatrofloxacin );
157605-25-9 (Alatrofloxacin Mesylate);
Chemical Name (1α, 5α, 6α)-L-alanyl-N-[3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridine-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninamide, monomethanesulfonate

Research Code:CP-116517-27; CP-116517,    Trade Name:Trovan I.V.®          MOA:Quinolone antibiotic            Indication:Life- or limb-threatening infections caused by susceptible strains          Status:Withdrawn    Company:Pfizer (Originator)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.[1]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001

Alatrofloxacin mesylate was first approved by the U.S. Food and Drug Administration (FDA) on Dec 18, 1997. It was developed and marketed as Trovan I.V. ® by Pfizer in the US.

Alatrofloxacin mesylate is a fluoronaphthyridone related to the fluoroquinolones with in vitro activity against a wide range of gram-negative and gram-positive aerobic and anaerobic microorganisms. The bactericidal action of alatrofloxacin results from inhibition of DNA gyrase and topoisomerase IV. Trovan I.V.® is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below.

Trovan I.V.® is available as injection solution for intravenous use, containing 7.86 mg/ml of Alatrofloxacin mesylate. The recommended starting dose is 200 mg or 300 mg administered intravenously.

Alatrofloxacin mesylate was withdrawn from the U.S. market in 2001.

Image result for Alatrofloxacin mesylate

Alatrofloxacin mesilate

    • Synonyms:CP 116517, CP 116517-27
    • ATC:J01MA
  • Use:antibiotic, prodrug of trovafloxacin
  • Chemical name:l-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-l-alaninamide monomethanesulfonate
  • Formula:C26H25F3N6O5 • CH4O3S
  • MW:654.62 g/mol
  • CAS-RN:146961-77-5

Derivatives

base

  • Formula:C26H25F3N6O5
  • MW:558.52 g/mol
  • CAS-RN:146961-76-4

Substance Classes

Synthesis Path

Substances Referenced in Synthesis Path

CAS-RN Formula Chemical Name CAS Index Name
27317-69-7 C11H20N2O5 Ntert-butoxycarbonyl-l-alanyl-l-alanine L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-
186772-86-1 C33H37F3N6O7 N-[(1,1-dimethylethoxy)carbonyl]-l-alanyl-N-[(1α,5α,6α)-3-[8-(2,4-difluorophenyl)-6-(ethoxycarbonyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-l-alaninamide L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-N-[(1α,5α,6α)-3-[8-(2,4-difluorophenyl)-6-(ethoxycarbonyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-
171176-56-0 C22H19F3N4O3 ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 1,8-Naphthyridine-3-carboxylic acid, 7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, ethyl ester, (1α,5α,6α)-
134575-66-9 C27H27F3N4O5 ethyl (1α,5α,6α)-1-(2,4-difluorophenyl)-7-[6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 1,8-Naphthyridine-3-carboxylic acid, 1-(2,4-difluorophenyl)-7-[6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-4-oxo-, ethyl ester, (1α,5α,6α)-
75-75-2 CH4O3S methanesulfonic acid Methanesulfonic acid

Trade Names

Country Trade Name Vendor Annotation
D TROVAN Pfizer wfm
F Turvel Pfizer wfm
GB Turvel Pfizer wfm
I Turvel Pfizer wfm
USA Trovan Pfizer wfm

(wfm = withdrawn from market)

Formulations

  • vial 200 mg/40 ml, 300 mg/60 ml (5 mg/ml) (as mesilate)

References

    • US 5 164 402 (Pfizer; 17.11.1992; appl. 4.2.1991; WO-prior. 16.8.1989).
    • US 5 229 396 (Pfizer; 20.7.1993; appl. 24.7.1992).
    • WO 9 700 268 (Pfizer; appl. 27.3.1996; USA-prior. 15.6.1995).
    • US 5 763 454 (Pfizer; 9.6.1998; appl. 21.5.1997; WO-prior. 6.6.1995).
  • polymorphs:

    • US 6 080 756 (Pfizer; 27.6.2000; appl. 30.1.1998; WO-prior. 5.7.1996).

References
“Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)” (PDF). Food and Drug Administration. Retrieved 29 August 2014.

Alatrofloxacin
Alatrofloxacin.svg
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a605016
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Intravenous
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
Bioavailability N/A
Protein binding 76% (trovafloxacin)
Metabolism Quickly hydrolyzed to trovafloxacin
Elimination half-life 9 to 12 hours (trovafloxacin)
Excretion Fecal and renal(trovafloxacin)
Identifiers
CAS Number
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C26H25F3N6O5
Molar mass 558.509 g/mol
3D model (JSmol)

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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 AFRICURE PHARMA as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 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, 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 32 PLUS year tenure till date Feb 2023, 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 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, 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 38 lakh plus views on New Drug Approvals Blog in 227 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 He has total of 32 International and Indian awards

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