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Cytarabine Hydrochloride

HCID 6252
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
69-74-9
Standard SMILES
Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
InChIKey
KCURWTAZOZXKSJ-JBMRGDGGSA-N
Molecular formula
C9H13N3O5.ClH
Average molar mass
279.68 g/mol
Monoisotopic mass
279.06219823

Overview

Crystals (from aqueous ethanol) or fluffy white powder. (NTP, 1992)

Names & identifiers

Preferred name
Cytarabine Hydrochloride
IUPAC
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
English name
1-beta-D-Arabinofuranosylcytosine hydrochloride
Molecular formula
C9H14ClN3O5
Molecular weight
279.68

Names & synonyms

CYTARABINE HYDROCHLORIDE69-74-9Cytosine arabinoside hydrochlorideCytarabine HCl1-beta-D-Arabinofuranosylcytosine hydrochlorideCytosar hydrochlorideSpongocytidine hydrochlorideArabitin hydrochlorideAracytidine hydrochlorideU-19920AIretinDTXSID5024891
Show more names
ARA-Cac1075ALEXANCylocideAra-c.HaCytarbineARA-C HCL
Aracytin hydrochlorideNSC-6387833K3DB65911-beta-D-Arabinofuranosylcytosine monohydrochlorideArabinosylcytosine hydrochlorideDTXCID104891Arabinofuranosylcytosine hydrochloride2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-, monohydrochloride

Database identifiers

CAS
69-74-9
PubChem CID
6252
DTXSID
DTXSID5024891
ChEMBL
CHEMBL1256472

Properties

Computed structural properties

Topological polar surface area
129 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
18
Formal charge
0
Complexity
383

Experimental & physicochemical properties

Solubility · 2 items

greater than or equal to 100 mg/mL at 63 °F (NTP, 1992)

>42 [ug/mL] (The mean of the results at pH 7.4)

Human DrugsBreast Feeding; Lactation; Milk, Human; Antimetabolites, Antineoplastic; Immunosuppressive Agents; Nucleosides
Melting Point356 to 360 °F (NTP, 1992)
Physical DescriptionCrystals (from aqueous ethanol) or fluffy white powder. (NTP, 1992)

Physicochemical properties

Melting point
197 · 197-198 °C(lit.)
storage temp.
2 · 2-8°C
solubility
14.2 mg/mL · insoluble in EtOH; ≥14.2 mg/mL in DMSO; ≥64.2 mg/mL in H2O
form
crystalline
color
White to off-white
biological source
synthetic (inorganic)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P318, P321, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 12-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21560
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this compound include leukopenia, thrombocytopenia, anemia, megaloblastosis, hepatic dysfunction, thromobophlebitis at the site of injection, and conjunctivitis. Other symptoms include potent bone marrow suppression, reduced reticulocytes, anorexia, nausea, vomiting, diarrhea, oral and anal inflammation or ulceration, fever, rash, bleeding (all sites), sepsis, pneumonia, cellulitis at injection site, skin ulceration, urinary retention, renal dysfunction, neuritis, neural toxicity, sore throat, esophageal ulceration, esophagitis, chest pain, bowel necrosis, abdominal pain, freckling, jaundice, dizziness, alopecia, allergic edema, anaphylaxis, pruritus, shortness of breath, urticaria and headache. "Flu-like" syndrome may occur. Joint pains may also occur. Eye irritation has been reported. Other eye effects include reversible glittering opacities, pain, punctuate epithelial keratitis and photophobia.

Reactive GroupAlcohols and Polyols

Chemistry & industry

Pharmacology

Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification · 3 items

Antimetabolites that are useful in cancer chemotherapy.

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.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Uses & manufacturing

UsesFor the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia.
Applications · 4 items

DescriptionCytosine beta-D-arabinofuranoside Hydrochloride is the salt form of Cytarabine, which is a selective inhibitor of DNA synthesis and is used as an antineoplastic and antiviral. Cytosine beta-D-arabinofuranoside Hydrochloride is used in chemotherapy for the treatment of white blood cells cancers such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma.

UsesInterferes with the synthesis of DNA

UsesAntiviral.

General DescriptionCrystals (from aqueous ethanol) or fluffy white powder.

Upstream & downstream products

Related reactions

4 records
New reaction record
HRID 858365 reaction equation
HRID 858365As productuspto-grants-2006_12
HRID 859116 reaction equation
HRID 859116As productuspto-grants-2006_12
HRID 1781981 reaction equation
HRID 1781981As productuspto-grants-2009_03
HRID 1987727 reaction equation
HRID 1987727As productuspto-grants-2009_06

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
33K3DB6591
EC Number
200-713-9
InChI
InChI=1/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/s3
InChIKey
KCURWTAZOZXKSJ-XKIMMOKZSA-N
SMILES
N1([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=CC(N)=NC1=O.[H]Cl |&1:1,3,6,8,r|
CAS DataBase Reference
69 · 69-74-9(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
ARA-C
FDA UNII
33 K3DB6591 · 33K3DB6591
EPA Substance Registry System
Cytarabine hydrochloride (69-74-9)
UNSPSC Code
12352202 · 12352202
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
317 · H317-H319-H341-H361
Precautionary statements
201 · P201-P280-P302+P352-P305+P351+P338-P308+P313
Hazard Codes
Xn
Risk Statements
36 · 36-43-63
Safety Statements
26 · 26-36/37
WGK Germany
3 · 3
RTECS
5500000 · HA5500000
HazardClass
IRRITANT
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Muta · Eye Irrit. 2Muta. 2Repr. 2Skin Sens. 1
Toxicity
50 oral · LD50 oral in rat: > 3200mg/kg
REACH Registrations
Active
Reactivity Profile
CYTARABINE HYDROCHLORIDE undergoes decomposition in acidic solutions.
Air and Water ReactionsWater soluble. Hydrolysis occurs readily, especially with acid.
Hazard Classes and CategoriesSkin Sens. 1 (100%)

Safety & protection

Fire FightingFires involving this material may 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.

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.

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

Exposure RoutesLess than 20% of the orally administered dose is absorbed from the gastrointestinal tract.
Toxicity Summary · 1 item

Cytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase) and under certain conditions blocking the progression of cells from the G1 phase to the S-phase. Although the mechanism of action is not completely understood, it appears that cytarabine acts through the inhibition of DNA polymerase. A limited, but significant, incorporation of cytarabine into both DNA and RNA has also been reported.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataCytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise.

Safety data

wgk
3
rtecs
HA5500000
hs_code
29389090
Toxicity
LD50 oral in rat: > 3200mg/kg
risk_code
36-43-63
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn
safety_code
26-36/37
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H317-H319-H341-H361
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Muta. 2Repr. 2Skin Sens. 1
Precautionary statements
P201-P280-P302+P352-P305+P351+P338-P308+P313

Upstream raw materials

ElectrophoresisEthanolLanthanum hydroxideCytarabineCytidineSodium hydroxideAncitabineAmmoniaMethanolHydrochloric acid

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
河北立业化学制品有限公司0310-6697998 13930001710 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
武汉凯威斯科技有限公司86-027-67849912 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
无锡中坤生化科技有限公司+86 0510-85629785
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
南京恰风和医药科技有限公司025-57018978 18251899859 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
上海皓骏医药科技有限公司021-34621078 13120882795 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
江苏欣德瑞医药科技有限公司18861302055 18861302055;18360347919 · [email protected]
杭州六可生物科技有限公司+86-571-86912261 19975279805 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
芜湖诺威化学技术有限公司0553-8233716 18055326116 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
襄阳美均机械技术检测有限公司13774177198 · [email protected]
保立基(南京)新材料科技有限公司18944488829 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
Beijing Yibai Biotechnology Co., Ltd0086-182-6772-3597 · [email protected]
康幸生物科技(上海)有限公司021-61556450 15800904410
上海岚克医药科技发展有限公司0086-21-58956006
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]