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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N3O3
Molecular Weight 211.2178
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZALCITABINE

SMILES

NC1=NC(=O)N(C=C1)[C@H]2CC[C@@H](CO)O2

InChI

InChIKey=WREGKURFCTUGRC-POYBYMJQSA-N
InChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1

HIDE SMILES / InChI
The nucleoside analog 2',3'-dideoxycytidine (ddCyd), also known as Zalcitabine is a nucleoside analog reverse transcriptase inhibitor (NRTI) sold under the trade name Hivid. HIVID is indicated in combination with antiretroviral agents for the treatment of HIV infection. It is used as part of a combination regimen with antiretroviral agents. But it was discontinued by Roche Pharmaceuticals on December 31, 2006 due to the availability of newer HIV medicines. Within cells, zalcitabine is converted to the active metabolite, dideoxycytidine 5'-triphosphate (ddCTP), by the sequential action of cellular enzymes. Dideoxycytidine 5'-triphosphate inhibits the activity of the HIV-reverse transcriptase both by competing for utilization of the natural substrate, deoxycytidine 5'-triphosphate (dCTP), and by its incorporation into viral DNA. The lack of a 3'- OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation and, therefore, the viral DNA growth is terminated. The active metabolite, ddCTP, is also an inhibitor of cellular DNA polymerasebeta and mitochondrial DNA polymerase-gamma and has been reported to be incorporated into the DNA of cells in culture.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HIVID

Approved Use

HIVID is indicated in combination with antiretroviral agents for the treatment of HIV infection. This indication is based on study results showing a reduction in the rate of disease progression (AIDS-defining events or death) in patients with limited prior antiretroviral therapy who were treated with the combination of HIVID and zidovudine. This indication is also based on a study showing a reduction in both mortality and AIDS-defining clinical events for patients who received INVIRASE® (saquinavir mesylate) in combination with HIVID compared to patients who received either HIVID or INVIRASE alone.

Launch Date

7.0891202E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.6 μg/L
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
10.5 μg/L
0.5 mg single, intravenous
dose: 0.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
79 μg/L
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9.3 μg/L
0.02 mg/kg bw single, oral
dose: 0.02 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
15.5 ng/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FED
25.2 ng/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.018 mg × h/L
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.022 mg × h/L
0.5 mg single, intravenous
dose: 0.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.208 mg × h/L
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.025 mg × h/L
0.02 mg/kg bw single, oral
dose: 0.02 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
62 ng × h/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FED
72 ng × h/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.3 h
0.5 mg single, intravenous
dose: 0.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.8 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.4 h
0.02 mg/kg bw single, oral
dose: 0.02 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
2 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FED
2 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
96%
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FED
96%
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALCITABINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
0.09 mg/kg 6 times / day multiple, oral
Dose: 0.09 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.09 mg/kg, 6 times / day
Sources: Page: p.858
unhealthy, 26-57
n = 5
Health Status: unhealthy
Condition: HIV infection
Age Group: 26-57
Sex: M
Population Size: 5
Sources: Page: p.858
Disc. AE: Peripheral neuropathy, Leukopenia...
AEs leading to
discontinuation/dose reduction:
Peripheral neuropathy (40%)
Leukopenia (20%)
Thrombocytopenia (40%)
Sources: Page: p.858
0.06 mg/kg 6 times / day multiple, oral
Highest studied dose
Dose: 0.06 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.06 mg/kg, 6 times / day
Sources: Page: p.191
unhealthy, 42
n = 18
Health Status: unhealthy
Condition: HIV infection
Age Group: 42
Sex: M+F
Population Size: 18
Sources: Page: p.191
Disc. AE: Peripheral neuropathy...
AEs leading to
discontinuation/dose reduction:
Peripheral neuropathy (grade 3, 100%)
Sources: Page: p.191
0.03 mg/kg 6 times / day multiple, oral
Dose: 0.03 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.03 mg/kg, 6 times / day
Sources: Page: p.191
unhealthy, 42
n = 18
Health Status: unhealthy
Condition: HIV infection
Age Group: 42
Sex: M+F
Population Size: 18
Sources: Page: p.191
Disc. AE: Peripheral neuropathy...
AEs leading to
discontinuation/dose reduction:
Peripheral neuropathy (grade 3, 100%)
Sources: Page: p.191
1.5 mg 3 times / day multiple, oral
Overdose
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Other AEs: Peripheral neuropathy...
Other AEs:
Peripheral neuropathy (80%)
Sources: Page: p.18
4.5 mg 3 times / day multiple, oral
Overdose
Dose: 4.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 4.5 mg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Other AEs: Peripheral neuropathy...
Other AEs:
Peripheral neuropathy (100%)
Sources: Page: p.18
0.25 mg/kg 3 times / day multiple, oral
Overdose
Dose: 0.25 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 0.25 mg/kg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Disc. AE: Rash, Fever...
AEs leading to
discontinuation/dose reduction:
Rash
Fever
Sources: Page: p.18
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.1
Other AEs: Peripheral neuropathy...
Other AEs:
Peripheral neuropathy (grade 3-5)
Sources: Page: p.1
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.1, p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.1, p.7
Other AEs: Lactic acidosis, Hepatic steatosis...
Other AEs:
Lactic acidosis (grade 3-5)
Hepatic steatosis (grade 3-5)
Hepatic failure (grade 3-5)
Sources: Page: p.1, p.7
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Other AEs: Pancreatitis, Oral ulceration...
Other AEs:
Pancreatitis (grade 3-5, 1.1%)
Oral ulceration (grade 3, 3%)
Esophageal ulcer (grade 3)
Cardiomyopathy (grade 3, infrequent)
Congestive heart failure (grade 3, infrequent)
Anaphylactoid reaction (grade 3)
Sources: Page: p.7
AEs

AEs

AESignificanceDosePopulation
Leukopenia 20%
Disc. AE
0.09 mg/kg 6 times / day multiple, oral
Dose: 0.09 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.09 mg/kg, 6 times / day
Sources: Page: p.858
unhealthy, 26-57
n = 5
Health Status: unhealthy
Condition: HIV infection
Age Group: 26-57
Sex: M
Population Size: 5
Sources: Page: p.858
Peripheral neuropathy 40%
Disc. AE
0.09 mg/kg 6 times / day multiple, oral
Dose: 0.09 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.09 mg/kg, 6 times / day
Sources: Page: p.858
unhealthy, 26-57
n = 5
Health Status: unhealthy
Condition: HIV infection
Age Group: 26-57
Sex: M
Population Size: 5
Sources: Page: p.858
Thrombocytopenia 40%
Disc. AE
0.09 mg/kg 6 times / day multiple, oral
Dose: 0.09 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.09 mg/kg, 6 times / day
Sources: Page: p.858
unhealthy, 26-57
n = 5
Health Status: unhealthy
Condition: HIV infection
Age Group: 26-57
Sex: M
Population Size: 5
Sources: Page: p.858
Peripheral neuropathy grade 3, 100%
Disc. AE
0.06 mg/kg 6 times / day multiple, oral
Highest studied dose
Dose: 0.06 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.06 mg/kg, 6 times / day
Sources: Page: p.191
unhealthy, 42
n = 18
Health Status: unhealthy
Condition: HIV infection
Age Group: 42
Sex: M+F
Population Size: 18
Sources: Page: p.191
Peripheral neuropathy grade 3, 100%
Disc. AE
0.03 mg/kg 6 times / day multiple, oral
Dose: 0.03 mg/kg, 6 times / day
Route: oral
Route: multiple
Dose: 0.03 mg/kg, 6 times / day
Sources: Page: p.191
unhealthy, 42
n = 18
Health Status: unhealthy
Condition: HIV infection
Age Group: 42
Sex: M+F
Population Size: 18
Sources: Page: p.191
Peripheral neuropathy 80%
1.5 mg 3 times / day multiple, oral
Overdose
Dose: 1.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Peripheral neuropathy 100%
4.5 mg 3 times / day multiple, oral
Overdose
Dose: 4.5 mg, 3 times / day
Route: oral
Route: multiple
Dose: 4.5 mg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Fever Disc. AE
0.25 mg/kg 3 times / day multiple, oral
Overdose
Dose: 0.25 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 0.25 mg/kg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Rash Disc. AE
0.25 mg/kg 3 times / day multiple, oral
Overdose
Dose: 0.25 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 0.25 mg/kg, 3 times / day
Sources: Page: p.18
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.18
Peripheral neuropathy grade 3-5
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.1
Hepatic failure grade 3-5
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.1, p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.1, p.7
Hepatic steatosis grade 3-5
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.1, p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.1, p.7
Lactic acidosis grade 3-5
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.1, p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.1, p.7
Anaphylactoid reaction grade 3
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Esophageal ulcer grade 3
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Oral ulceration grade 3, 3%
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Cardiomyopathy grade 3, infrequent
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Congestive heart failure grade 3, infrequent
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Pancreatitis grade 3-5, 1.1%
0.75 mg 3 times / day multiple, oral
Recommended
Dose: 0.75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 0.75 mg, 3 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: HIV infection
Sources: Page: p.7
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
not determined
PubMed

PubMed

TitleDatePubMed
Human immunodeficiency virus 1 strains resistant to nucleoside inhibitors of reverse transcriptase in isolates from the Czech Republic as monitored by line probe assay and nucleotide sequencing.
2001
Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure.
2001
DABOs as candidates to prevent mucosal HIV transmission.
2001
The molecular basis of inhibition and toxicity of modified cytosine analogues targetting HIV-1 reverse transcriptase.
2001
Peripheral neuropathy during stavudine-didanosine antiretroviral therapy.
2001 Apr
Synthesis and antiviral evaluation of C-4-hydrazide derivatives of 2',3'-dideoxycytidine.
2001 Apr-Jul
Testing the reverse transcriptase model of somatic mutation.
2001 Aug
Do HIV type 1 RNA levels provide additional prognostic value to CD4(+) T lymphocyte counts in patients with advanced HIV type 1 infection?
2001 Aug 10
Susceptibility of human T cell leukemia virus type 1 to reverse-transcriptase inhibitors: evidence for resistance to lamivudine.
2001 Aug 15
[Therapeutic aspects of HIV/AIDS infected patients and evaluation of therapeutic protocols].
2001 Dec
HIV-1 reverse transcriptase mutations found in a drug-experienced patient confer reduced susceptibility to multiple nucleoside reverse transcriptase inhibitors.
2001 Dec
Antiviral activity of NMSO3 against adenovirus in vitro.
2001 Dec
MIKADO: a multicentre, open-label pilot study to evaluate the antiretroviral activity and safety of saquinavir with stavudine and zalcitabine.
2001 Jan
Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases.
2001 Jan-Feb
Differential susceptibility of retroviruses to nucleoside analogues.
2001 Mar
Mitochondrial alterations with mitochondrial DNA depletion in the nerves of AIDS patients with peripheral neuropathy induced by 2'3'-dideoxycytidine (ddC).
2001 Nov
New developments in anti-HIV chemotherapy.
2001 Nov
Anti-human immunodeficiency virus drugs are ineffective against Pneumocystis carinii in vitro and in vivo.
2001 Nov 15
HIV-protease inhibitors alter retinoic acid synthesis.
2001 Oct 19
Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells.
2001 Sep
Antitumor activity of 2',3'-dideoxycytidine nucleotide analog against tumors up-regulating DNA polymerase beta.
2001 Sep
A preliminary benefit-risk assessment of lamivudine for the treatment of chronic hepatitis B virus infection.
2002
"Senseless" antiviral polyribonucleotides: poly (1-propargylinosinic acid).
2002
Novel direct detection method for quantitative determination of intracellular nucleoside triphosphates using weak anion exchange liquid chromatography/tandem mass spectrometry.
2002
Fomivirsen: clinical pharmacology and potential drug interactions.
2002
The dangers of inferring treatment effects from observational data: a case study in HIV infection.
2002 Apr
Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir.
2002 Apr
Tenofovir exhibits low cytotoxicity in various human cell types: comparison with other nucleoside reverse transcriptase inhibitors.
2002 Apr
Broad nucleoside-analogue resistance implications for human immunodeficiency virus type 1 reverse-transcriptase mutations at codons 44 and 118.
2002 Apr 1
Molecular basis of 2',3'-dideoxycytidine-induced drug resistance in human cells.
2002 Feb
The distribution of the anti-HIV drug, 2'3'-dideoxycytidine (ddC), across the blood-brain and blood-cerebrospinal fluid barriers and the influence of organic anion transport inhibitors.
2002 Feb
Involvement of DNA polymerase beta in DNA replication and mutagenic consequences.
2002 Feb 1
Viral and immunologic follow up of 4 to 9 years of AIDS treatments by quadruple combinations of virostatics including integrase inhibitors applied in short sequences differing by drug rotation.
2002 Jan
Uptake of lamivudine by rat renal brush border membrane vesicles.
2002 Jan
Transbuccal delivery of 2',3'-dideoxycytidine: in vitro permeation study and histological investigation.
2002 Jan 1
ATP-dependent removal of nucleoside reverse transcriptase inhibitors by human immunodeficiency virus type 1 reverse transcriptase.
2002 Jul
An ancient prevertebrate Na+-nucleoside cotransporter (hfCNT) from the Pacific hagfish (Eptatretus stouti).
2002 Jul
3'-Azido-2',3'-dideoxythymidine induced deficiency of thymidine kinases 1, 2 and deoxycytidine kinase in H9 T-lymphoid cells.
2002 Jul 15
Perspectives on the molecular mechanism of inhibition and toxicity of nucleoside analogs that target HIV-1 reverse transcriptase.
2002 Jul 18
New developments in anti-HIV chemotherapy.
2002 Jul 18
Prevalence of HIV-1 polymerase gene mutations in pre-treated patients in Thailand.
2002 Mar
Observations of HIV-1 genotypic drug resistance in a trial of four reverse transcriptase inhibitors (Quattro Trial).
2002 Mar
ViroLogic announces agreement with Achillion.
2002 Mar
Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent.
2002 Mar
Assessment of mitochondrial toxicity in human cells treated with tenofovir: comparison with other nucleoside reverse transcriptase inhibitors.
2002 Mar
Dietary supplements in the treatment of nucleoside reverse transcriptase inhibitor-related mitochondrial toxicity.
2002 Mar 29
Concurrent analysis of nucleoside reverse transcriptase inhibitors in a pool of endogenous nucleosides by short-end injection-capillary electrochromatography on a beta-cyclodextrin-bonded stationary phase.
2002 May
Certification of the critical importance of L-3-(2-naphthyl)alanine at position 3 of a specific CXCR4 inhibitor, T140, leads to an exploratory performance of its downsizing study.
2002 May
Impact of highly active antiretroviral therapy on cognitive processing in HIV infection: cross-sectional and longitudinal studies of event-related potentials.
2002 May 1
Point mutations and deletions in the znfn1a1/ikaros gene in chemically induced murine lymphomas.
2002 May 1
Patents

Sample Use Guides

Patients should be advised that HIVID is recommended for use in combination with active antiretroviral therapy. Greater activity has been observed when new antiretroviral therapies are begun at the same time as HIVID. Concomitant therapy should be based on a patient’s prior drug exposure. The recommended regimen is one 0.750 mg tablet of HIVID orally every 8 hours (2.25 mg HIVID total daily dose) in combination with other antiretroviral agents. Please refer to the complete product information for each of the other antiretroviral agents for the recommended doses of these agents. Based on preliminary data, the recommended HIVID dosage reduction for patients with impaired renal function is: creatinine clearance 10 to 40 mL/min: 0.750 mg of HIVID every 12 hours; creatinine clearance <10 mL/min: 0.750 mg of HIVID every 24 hours.
Route of Administration: Oral
In Vitro Use Guide
2',3'-Dideoxycytidine (DDC) was evaluated for prophylactic antiviral activity in vitro using the feline leukemia virus (FeLV)-cat animal model. In vitro antiviral activity of DDC against FeLV was dependent upon the target cell used for infection. DDC (5 to 10 microM) inhibited FeLV infection of feline lymphoid cells by greater than 80%, while 6.07 to 12.13 uM DDC was required to similarly inhibit infection of feline fibroblasts. However, 43 to 384 uM DDC was needed to inhibit FeLV infection of primary bone marrow cells by greater than 80%. These in vitro results suggest that, although relatively low doses of DDC may be adequate to prevent infection of feline lymphoid cells, 8- to 80-times-higher doses may be necessary to block infection of bone marrow cells, a primary target cell type for FeLV infection. Results of in vitro studies suggest that feline bone marrow cells may remain partially susceptible to FeLV infection at tolerated doses, while other somatic target tissues (i.e., lymphoid or epithelial tissues) may be protected from infection.
Name Type Language
ZALCITABINE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
ZALCITABINE [USAN]
Common Name English
ZALCITABINE [ORANGE BOOK]
Common Name English
2',3'-DIDEOXYCYTIDINE
Systematic Name English
RO 24-2027/000
Code English
ZALCITABINE [HSDB]
Common Name English
ZALCITABINE [JAN]
Common Name English
ZALCITABINE (DIDEOXYCYTIDINE,DDC) [VANDF]
Common Name English
RO-24-2027/000
Code English
HIVID
Brand Name English
Zalcitabine [WHO-DD]
Common Name English
NSC-606170
Code English
ZALCITABINE [IARC]
Common Name English
ZALCITABINE [USP-RS]
Common Name English
DIDEOXYCYTIDINE
Systematic Name English
RO-242027000
Code English
ZALCITABINE [MART.]
Common Name English
ZALCITABINE [VANDF]
Common Name English
DDC
Common Name English
CYTIDINE, 2',3'-DIDEOXY-
Systematic Name English
zalcitabine [INN]
Common Name English
ZALCITABINE [MI]
Common Name English
RO-24-2027000
Code English
ZALCITABINE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ05AF03
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
WHO-ATC J05AF03
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
FDA ORPHAN DRUG 17586
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
FDA ORPHAN DRUG 28388
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
NCI_THESAURUS C1557
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
LIVERTOX 1044
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID0023747
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
USAN
CC-48
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
RS_ITEM_NUM
1724306
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
WIKIPEDIA
ZALCITABINE
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
PUBCHEM
24066
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
DAILYMED
6L3XT8CB3I
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
NSC
606170
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
ChEMBL
CHEMBL853
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
MERCK INDEX
M11577
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY Merck Index
FDA UNII
6L3XT8CB3I
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
RXCUI
3363
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY RxNorm
NCI_THESAURUS
C430
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
INN
6871
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
DRUG BANK
DB00943
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
MESH
D016047
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
CHEBI
10101
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
DRUG CENTRAL
2856
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
IUPHAR
4828
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
CAS
7481-89-2
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY
EVMPD
SUB00130MIG
Created by admin on Sat Dec 17 18:29:10 UTC 2022 , Edited by admin on Sat Dec 17 18:29:10 UTC 2022
PRIMARY