Details of the Drug

General Information of Drug (ID: DM9UCJK)

• Drug Name: Doripenem
• Synonyms: Doribax; S 4661; S-4661; Doripenem (USAN/INN); (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Cholecystitis	N.A.	Approved	[1]
Pyelonephritis	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[2]
Gram-positive bacterial infection	1B74-1G40	Phase 3	[3]

• Affected Organisms: AcinetobacterEscherichia coliKlebsiellaProteus mirabilisPseudomonas aeruginosaStreptococcus constellatusVarious aerobic and anaerobic microorganismsStreptococcus pneumoniaeStaphylococcus aureusEnterococcus faecalisEnterococcus faeciumEnterobacterHaemophilus influenzaeMoraxella catarrhalis
• ATC Code:
  J01DH04: Doripenem
  J01DH: Carbapenems
  J01D: OTHER BETA-LACTAM ANTIBACTERIALS
  J01: ANTIBACTERIALS FOR SYSTEMIC USE
  J: ANTIINFECTIVES FOR SYSTEMIC USE
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 420.5
  Logarithm of the Partition Coefficient (xlogp); -3.4
  Rotatable Bond Count (rotbonds); 7
  Hydrogen Bond Donor Count (hbonddonor); 5
  Hydrogen Bond Acceptor Count (hbondacc); 10
• ADMET Property:
  Clearance: The clearance of drug is 10.3 L/h []
  Half-life: The concentration or amount of drug in body reduced by one-half in 1 hour [4]
  Metabolism: The drug is metabolized via the dehydropeptidase-I into a microbiologically inactive ring-opened metabolite doripenem-M1 []
  Unbound Fraction: The unbound fraction of drug in plasma is 0.92% [4]
  Vd: The volume of distribution (Vd) of drug is 16.8 L []
• Chemical Identifiers:
  Formula: C15H24N4O6S2
  IUPAC Name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  Canonical SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O
  InChI: InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1
  InChIKey: AVAACINZEOAHHE-VFZPANTDSA-N
• Cross-matching ID:
  PubChem CID: 73303
  ChEBI ID: CHEMBL491571
  CAS Number: 148016-81-3
  UNII: BHV525JOBH
  DrugBank ID: DB06211
  TTD ID: D03QWT
  INTEDE ID: DR0534
• Drug-Molecule Activity Atlas (DMA)NEW: Click to Jump to the Detailed DMA Information of This Drug
• Drug ADMET Endpoint Profile (DAE)NEW: Click to Jump to the Detailed DAE Information of This Drug
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Dihydropteroate synthetase (Bact folP)	TT4ILYC	DHPS_ECOLI	Inhibitor	[3]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dehydropeptidase-I (DPEP1)	DEAMVR3	DPEP1_HUMAN	Substrate	[5]
Beta-lactamase (blaB)	DEC3G7M	A0A1S7IV31_ENTAS	Substrate	[6]

References

• [1] Doripenem FDA Label
• [2] 2007 FDA drug approvals: a year of flux. Nat Rev Drug Discov. 2008 Feb;7(2):107-9.
• [3] Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
• [4] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [5] Disposition, metabolism, and excretion of [14C]doripenem after a single 500-milligram intravenous infusion in healthy men. Antimicrob Agents Chemother. 2008 Oct;52(10):3478-83.
• [6] FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.