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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N3O3
Molecular Weight 211.2182
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZALCITABINE

SMILES

C1C[C@]([H])(n2ccc(=N)nc2O)O[C@]1([H])CO

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
Effect of nucleoside analogs and non-nucleoside inhibitors of HIV-1 reverse transcriptase on cell-free virions.
1999
Synthesis and antiviral activity of 1-[1,5-dialkyl-1H-1,2,4-triazol-3-yl)methyl]thymines.
1999 Apr
ddC- and 3TC-bis(SATE) monophosphate prodrugs overcome cellular resistance mechanisms to HIV-1 associated with cytidine kinase deficiency.
1999 Apr-May
"Mixed inhibitors" of HIV-reverse transcriptase: synthesis and antiviral activity.
1999 Apr-May
Molecular mechanism of the short-term cardiotoxicity caused by 2',3'-dideoxycytidine (ddC): modulation of reactive oxygen species levels and ADP-ribosylation reactions.
1999 Dec 15
Relation of peripheral neuropathy to HIV treatment in four randomized clinical trials including didanosine.
1999 Jul
Mechanism of action and in vitro activity of 1',3'-dioxolanylpurine nucleoside analogues against sensitive and drug-resistant human immunodeficiency virus type 1 variants.
1999 Oct
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.
2000 Dec
In vitro selection of mutations in the human immunodeficiency virus type 1 reverse transcriptase that decrease susceptibility to (-)-beta-D-dioxolane-guanosine and suppress resistance to 3'-azido-3'-deoxythymidine.
2000 Jul
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
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
Synthesis and antiviral evaluation of C-4-hydrazide derivatives of 2',3'-dideoxycytidine.
2001 Apr-Jul
[Therapeutic aspects of HIV/AIDS infected patients and evaluation of therapeutic protocols].
2001 Dec
Antiviral activity of NMSO3 against adenovirus in vitro.
2001 Dec
Synthesis and chain length-anti-HIV activity relationship of fully N- and O-sulfated homooligomers of tyrosine.
2001 Feb
Antiretroviral treatments used among adults with HIV infection in Europe.
2001 Feb
MIKADO: a multicentre, open-label pilot study to evaluate the antiretroviral activity and safety of saquinavir with stavudine and zalcitabine.
2001 Jan
Phosphorylation of nucleoside analog antiretrovirals: a review for clinicians.
2001 Jan
Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers.
2001 Jan
In vitro biological activity of prenylflavanones.
2001 Jan-Feb
Biological activity of kiwifruit peel extracts.
2001 Jun
Crystal structures of a ddATP-, ddTTP-, ddCTP, and ddGTP- trapped ternary complex of Klentaq1: insights into nucleotide incorporation and selectivity.
2001 Jun
Analysis of human immunodeficiency virus type 1 drug resistance in children receiving nucleoside analogue reverse-transcriptase inhibitors plus nevirapine, nelfinavir, or ritonavir (Pediatric AIDS Clinical Trials Group 377).
2001 Jun 15
Human cytosolic 5'-nucleotidase I: characterization and role in nucleoside analog resistance.
2001 Mar 30
Therapeutic effects of nucleoside analogues on psychomotor slowing in HIV infection.
2001 Mar 9
Differential human immunodeficiency virus-suppressive activity of reverse transcription inhibitors in resting and activated peripheral blood lymphocytes: implications for therapy.
2001 May-Jun
Mitochondrial alterations with mitochondrial DNA depletion in the nerves of AIDS patients with peripheral neuropathy induced by 2'3'-dideoxycytidine (ddC).
2001 Nov
Antitumor activity of 2',3'-dideoxycytidine nucleotide analog against tumors up-regulating DNA polymerase beta.
2001 Sep
"Senseless" antiviral polyribonucleotides: poly (1-propargylinosinic acid).
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
Broad nucleoside-analogue resistance implications for human immunodeficiency virus type 1 reverse-transcriptase mutations at codons 44 and 118.
2002 Apr 1
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
S-acyl-2-thioethyl (SATE) pronucleotides are potent inhibitors of HIV-1 replication in T-lymphoid cells cross-resistant to deoxycytidine and thymidine analogs.
2002 Feb
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
ATP-dependent removal of nucleoside reverse transcriptase inhibitors by human immunodeficiency virus type 1 reverse transcriptase.
2002 Jul
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
ZALCITABINE [WHO-DD]
Common 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
NSC-606170
Code English
ZALCITABINE [IARC]
Common Name English
ZALCITABINE [USP]
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
Classification Tree Code System Code
WHO-VATC QJ05AF03
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
WHO-ATC J05AF03
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
FDA ORPHAN DRUG 17586
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
FDA ORPHAN DRUG 28388
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
NCI_THESAURUS C1557
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
LIVERTOX 1044
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
Code System Code Type Description
EPA CompTox
7481-89-2
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
WIKIPEDIA
ZALCITABINE
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
USP_CATALOG
1724306
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY USP-RS
PUBCHEM
24066
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL853
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
MERCK INDEX
M11577
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY Merck Index
FDA UNII
6L3XT8CB3I
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
RXCUI
3363
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C430
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
INN
6871
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
DRUG BANK
DB00943
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
MESH
D016047
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
DRUG CENTRAL
2856
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
IUPHAR
4828
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
CAS
7481-89-2
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY
EVMPD
SUB00130MIG
Created by admin on Sat Jun 26 00:39:30 UTC 2021 , Edited by admin on Sat Jun 26 00:39:30 UTC 2021
PRIMARY