Dideoxyadenosine
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Dideoxyadenosine
structure -
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CAS No:
4097-22-7
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Formula:
C10H13N5O2
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Chemical Name:
Dideoxyadenosine
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Synonyms:
Adenosine,2′,3′-dideoxy-;2′,3′-Dideoxyadenosine;Dideoxyadenosine;NSC 98700;NQZ-047;117174-26-2;6699-71-4
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CAS No:
Description
2',3'-Dideoxyadenosine is an inhibitor of HIV replication[1]. Antiretroviral activity[1]. Antiviral efficacy[1].
2',3'-dideoxyadenosine is an off-white powder. (NTP, 1992)
2',3'-dideoxyadenosine is an off-white powder. (NTP, 1992)|2',3'-dideoxyadenosine is a purine 2',3'-dideoxyribonucleoside in which the nucleobase component is specified as adenine. It has a role as an EC 4.6.1.1 (adenylate cyclase) inhibitor and an EC 3.5.4.4 (adenosine deaminase) inhibitor. It is a purine 2',3'-dideoxyribonucleoside and a member of adenosines.|Dideoxyadenosine is a prodrug form of didanosine, a nucleoside reverse transcriptase inhibitor analog of adenosine.|A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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 an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.
Characteristics
99.1
-0.2
White to Off-white Powder
1.8±0.1 g/cm3
184-186 °C
539.1°C at 760 mmHg
279.9±32.9 °C
1.822
43.2g/L(25 ºC)
2-8°C
LD50 oral in mouse: 5gm/kg
D25 -25.2° (c = 1.01 in water)
Water soluble.
Alcohols and Polyols
2',3'-DIDEOXYADENOSINE may be sensitive to prolonged exposure to light.
Safety Information
NONH for all modes of transport
2
34-36/37-22
26-27-36/37/39-45-24/25
AU7358900
C
Bulk: 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.
P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
|Warning|H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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)
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)
Drug Information
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) (See all compounds classified as Antimetabolites.)|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. (See all compounds classified as Antiviral Agents.)
SYMPTOMS: 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)
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)
2',3' Dideoxyadenosine
Computed Properties
Molecular Weight:235.24
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:235.10692467
Monoisotopic Mass:235.10692467
Topological Polar Surface Area:99.1
Heavy Atom Count:17
Complexity:279
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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