Dideoxyadenosine

HCID 20039

Basic information

CAS
4097-22-7
Standard SMILES
Nc1ncnc2c1ncn2[C@H]1CC[C@@H](CO)O1
InChIKey
WVXRAFOPTSTNLL-NKWVEPMBSA-N
Molecular formula
C10H13N5O2
Average molar mass
235.24 g/mol
Monoisotopic mass
235.10692467

Names & identifiers

Preferred name
Dideoxyadenosine
IUPAC
[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol
English name
Dideoxyadenosine
Molecular formula
C10H13N5O2
Molecular weight
235.24

Names & synonyms

2',3'-Dideoxyadenosine4097-22-7dideoxyadenosineADENOSINE, 2',3'-DIDEOXY-ddAdoNSC-98700NSC 98700DTXSID20237714Q86AH641A2'-3'-dideoxyadenosineDTXCID203771CHEBI:91207
Show more names
DDA2',3'-ddADidanosin EP Imp GDDA, antiviral drug2’,3’-dideoxy-adenosin2', 3'-DideoxyadenosineDidanosine EP Impurity G
NSC98700ddA (Antiviral)2',3' DideoxyadenosineRefChem:1332886-amino-9-(2',3'-dideoxy-beta-D-glycero-pentofuranosyl)purine6-Amino-9-(2''3'-dideoxy-beta-D-glycero-pentofuranosyl)purine9-(2,3-DIDEOXY-BETA-D-GLYCERO-PENTOFURANOSYL)-9H-PURIN-6-AMINE223-853-2

Database identifiers

CAS
4097-22-7
PubChem CID
20039
DTXSID
DTXSID2023771
ChEMBL
CHEMBL14925、CHEMBL23094
ChEBI
CHEBI:91207
UNII
4Q86AH641A
EC Number
223-853-2
Nikkaji
J80.745A

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
99.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
2
Heavy atoms
17

Experimental & physicochemical properties

Solubility · 6 items

10 to 50 mg/mL at 68 °F (NTP, 1992)

H2O 3.4-5.1 (mg/mL)

Buffer, pH4 4.8-9.6 (mg/mL)

Buffer, pH9 3.2-4.8 (mg/mL)

EtOH 1.6-2.0 (mg/mL)

DMA 2.6-3.4 (mg/mL)

Melting Point358 to 363 °F (NTP, 1992)
Optical Rotation(c = 1 , H2O) [a]25 D = -28 ± 2°
Physical Description2',3'-dideoxyadenosine is an off-white powder. (NTP, 1992)
Stability/Shelf LifeBulk: 2',3'-Dideoxyadenosine is stable as a bulk chemical for at least 6 weeks at room temperature and 45 °C, under light or dark conditions. Solution: DDA was stable as a 0.1 mg/mL water solution for at least 23 hrs at room temperature.

Physicochemical properties

Melting point
181 · 181-184 °C(lit.)
alpha
25 · D25 -25.2° (c = 1.01 in water)
Boiling point
377.64 °C · 377.64°C (rough estimate)
Density
1.2455 · 1.2455 (rough estimate)
refractive index
-34 ° · -34 ° (C=1, H2O)
storage temp.
-20 °C · -20°C

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H341 (50%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to a related compound include cutaneous eruptions, fever, mouth sores, thrombocytopenia, neutropenia, reversible peripheral neuropathy, gastrointestinal distress, headache, nausea and vomiting. (NTP, 1992)
Reactive GroupAlcohols and Polyols;Amines, Phosphines, and Pyridines;Ethers
Reactivity Profile2',3'-DIDEOXYADENOSINE may be sensitive to prolonged exposure to light.
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesMuta. 2 (50%)

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a freezer. (NTP, 1992)

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Toxicity Data · 2 items

Mouse(po): LD50: 5 gm/kg

Mouse(sc): LD50: 1320 mg/kg

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
rtecs
AU7358900
hs_code
29349990
Toxicity
LD50 oral in mouse: 5gm/kg
risk_code
34-36/37-22

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Applications · 5 items

UsesDideoxy Adenosine (Didanosine EP Impurity G) is a potent anti-HIV agent.

Uses2′,3′-Dideoxyadenosine (ddA), a specific adenylyl cyclase inhibitor, is useful in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation.

UsesA potent labelled anti-HIV agent.

UsesA potent anti-HIV agent.

General DescriptionOff-white powder.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Additional notes

DefinitionChEBI: A purine 2',3'-dideoxyribonucleoside in which the nucleobase component is specified as adenine.

Related reactions

4 records

Compound notes

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