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Merck

D5782

2′,3′-Dideoxycytidine

≥98% (HPLC), synthetic (organic), powder

Synonym(s):

ddC

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About This Item

Empirical Formula (Hill Notation):
C9H13N3O3
CAS Number:
7481-89-2
Molecular Weight:
211.22
NACRES:
NA.52
PubChem Substance ID:
24278377
UNSPSC Code:
41106305
MDL number:
MFCD00012188
Beilstein/REAXYS Number:
654956
Assay:
≥98% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless to faintly yellow
Storage temp.:
−20°C

Key Documents

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Product Name

2′,3′-Dideoxycytidine, ≥98% (HPLC)

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

SMILES string

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

InChI key

WREGKURFCTUGRC-POYBYMJQSA-N

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

Quality Level

200

feature

PCR Additives

technique(s)

PCR: suitable

color

colorless

input

crude DNA

mp

217-218 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

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Application

2′,3′-Dideoxycytidine is used:
  • as a DNA chain-terminating nucleotide for DNA sequencing methods based on the Sanger chain-termination method
  • as a nucleoside reverse transcriptase inhibitor (NRTI) to study its effects on the development of mechanical allodynia in aging mice
  • as a mitochondrial DNA (mtDNA) replication inhibitor to inhibit the activation of cGAS-STING pathway and study its effects on signaling protein-stimulator of interferon genes (STING), cyclic GMP-AMP synthase (cGAS), and phospho-interferon regulator factor 3 (p-IRF3) expression in mouse hippocampal and microglial cells
  • as an NRTI inhibitor to study its effects on the drug induced-mitochondrial toxicity in Caenorhabditis elegans

Biochem/physiol Actions

2′,3′-Dideoxycytidine (ddC), is an ionic compound and a nucleoside analog. It acts as a nucleoside reverse transcriptase inhibitor and exhibits therapeutic effects against human immunodeficiency virus (HIV) infection. 2′,3′-Dideoxycytidine possesses anti-adenovirus activity and inhibits the adenovirus polymerase.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351

pcodes

P281

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

D5782-100MG: + D5782-BULK: + D5782-500MG: + D5782-VAR: + D5782-250MG:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7173V
WXBF6509V
WXBF5210V
WXBF4536V
WXBF4775V

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Shuang-Xi Gu et al.
Bioorganic & medicinal chemistry, 19(17), 5117-5124 (2011-08-10)
A series of 26 diarylpyrimidines, characterized by the hydroxymethyl linker between the left wing benzene ring and the central pyrimidine, were synthesized and evaluated for in vitro anti-HIV activity. Most of the compounds exhibited moderate to excellent activities against wild-type
Alexander N Patananan et al.
Cell reports, 33(13), 108562-108562 (2020-12-31)
Generating mammalian cells with desired mitochondrial DNA (mtDNA) sequences is enabling for studies of mitochondria, disease modeling, and potential regenerative therapies. MitoPunch, a high-throughput mitochondrial transfer device, produces cells with specific mtDNA-nuclear DNA (nDNA) combinations by transferring isolated mitochondria from
Anindya Roy Chowdhury et al.
iScience, 23(8), 101370-101370 (2020-08-02)
This study shows that multiple modes of mitochondrial stress generated by partial mtDNA depletion or cytochrome c oxidase disruption cause ryanodine receptor channel (RyR) dysregulation, which instigates the release of Ca2+ in the cytoplasm of C2C12 myoblasts and HCT116 carcinoma
R Mentel et al.
Antiviral research, 47(2), 79-87 (2000-09-21)
The antiviral activity of 2',3'-dideoxycytidine (ddC) has been investigated in a mouse pneumonia model. Consolidation of lung, histopathological changes, DNA synthesis as well as levels of TNFalpha were assayed. In this in vivo model, the oral administration of ddC twice
Didier Desmaële et al.
Journal of controlled release : official journal of the Controlled Release Society, 161(2), 609-618 (2011-08-16)
Squalene is a triterpene widely distributed in nature that is an intermediate in the cholesterol biosynthesis pathway. The remarkable dynamic folded conformation of squalene has been used to chemically conjugate this lipid with various therapeutic molecules to construct nanoassemblies of
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