sparfloxacin

Trade name: zagam

Small moleculeapproved

Approved

Dec 19, 1996

Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription. Quinolones differ in chemical structure and mode of action from (beta)-lactam antibiotics. Quinolones may, therefore, be active against bacteria resistant to (beta)-lactam antibiotics. Although cross-resistance has been observed between sparfloxacin and other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to sparfloxacin. In vitro tests show that the combination of sparfloxacin and rifampin is antagonistic against Staphylococcus aureus. The bactericidal action of sparfloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination. Sparfloxacin is used for the treatment of adults with the following infections caused by susceptible strains microorganisms: community-acquired pneumonia (caused by Chlamydia pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, or Streptococcus pneumoniae) and acute bacterial exacerbations of chronic bronchitis (caused by Chlamydia pneumoniae, Enterobacter cloacae, Haemophilus influenzae, Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis,Staphylococcus aureus, or Streptococcus pneumoniae). Sparfloxacin has trade names Spacin in Bangladesh, Zagam and Zagam Respipac. Zagam is no longer available in the United States. — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 1 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Timeline

1990s

  1. Dec 19, 1996

    Mylan — Earliest FDA Approval

  2. Dec 19, 1996

    Mylan — NDA Organization

  3. Dec 19, 1996

    Mylan — NDA Secondary Org

Indications

Mechanism of action

Approval history

  • approvedDec 19, 1996

Chemistry & pharmacology

Loading structure…

SMILES

C[C@H]1CN(C[C@@H](C)N1)C2=C(F)C3=C(C(=O)C(=CN3C4CC4)C(O)=O)C(N)=C2F
Mol. weight
392.3998 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)- 6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  • at 4140
  • at-4140
  • at-4140
  • at-4140
  • at-4140
  • ci 978
  • ci-978
  • ci-978
  • ci-978
  • ci-978
  • cis-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  • cis-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  • pd 131501
  • pd 131501
  • pd-131501
  • spara
  • spara
  • sparcin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • sparfloxacin
  • zagam
  • zagam
  • zagam
  • zagam

Organizations

Marketing (2)

OrganizationOrg typeRelationshipDate
MylanFor profitNDADec 19, 1996
MylanFor profitNDA2Dec 19, 1996