zalcitabine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives 2856 7481-89-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • Ro 24-2027/000
  • hivid
  • zalcitabine
  • dideoxycytidine
A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.
  • Molecular weight: 211.22
  • Formula: C9H13N3O3
  • CLOGP: -1.25
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 88.15
  • ALOGS: -1.48
  • ROTB: 2

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2.25 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 76.40 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 65 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.15 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 88 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.54 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.96 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 19, 1992 FDA ROCHE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AF03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleoside and nucleotide reverse transcriptase inhibitors
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:36044 antiviral drugs
CHEBI has role CHEBI:53756 reverse transcriptase inhibitors
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D009676 Noxae
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
MeSH PA D018894 Reverse Transcriptase Inhibitors

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.13 acidic
pKa2 4.25 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Deoxycytidine kinase Kinase WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme INHIBITOR Ki 7.29 CHEMBL CHEMBL

External reference:

IDSource
4023282 VUID
N0000148230 NUI
D00412 KEGG_DRUG
4020505 VANDF
4023282 VANDF
C0012132 UMLSCUI
CHEBI:10101 CHEBI
CHEMBL853 ChEMBL_ID
DB00943 DRUGBANK_ID
D016047 MESH_DESCRIPTOR_UI
24066 PUBCHEM_CID
6871 INN_ID
4828 IUPHAR_LIGAND_ID
6L3XT8CB3I UNII
196461 RXNORM
5702 MMSL
810 MMSL
d00127 MMSL
003661 NDDF
34693000 SNOMEDCT_US
387187000 SNOMEDCT_US

Pharmaceutical products:

None