Clofarabine

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Names

[ CAS No. ]:
123318-82-1

[ Name ]:
Clofarabine

[Synonym ]:
Clofarex
(2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxyméthyl)tétrahydrofuran-3-ol
9H-Purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-
2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine
(2R,3R,4S,5R)-5-(6-Amino-2-chlor-9H-purin-9-yl)-4-fluor-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
2-chloro-2'-arabino-fluoro-2'-deoxyadenosine
Cl-F-Ara-A
Clofarabine
Clofarabine [USAN]
Clolar
2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine
MFCD00871077

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Boiling Point ]:
599.5±60.0 °C at 760 mmHg

[ Melting Point ]:
228-231 °C

[ Molecular Formula ]:
C10H11ClFN5O3

[ Molecular Weight ]:
303.677

[ Flash Point ]:
316.4±32.9 °C

[ Exact Mass ]:
303.053436

[ PSA ]:
119.31000

[ LogP ]:
0.24

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.844

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UD7473000
CHEMICAL NAME :
9H-Purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) -
CAS REGISTRY NUMBER :
123318-82-1
LAST UPDATED :
199706
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C10-H11-Cl-F-N5-O3
MOLECULAR WEIGHT :
303.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Leukocyte
DOSE/DURATION :
50 nmol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 51,2386,1991

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xi,C

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .

[ Safety Phrases ]:
S26-S36-S45-S36/37/39

[ RIDADR ]:
UN 2735 8/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
DP5550000

[ Packaging Group ]:
III

[ Hazard Class ]:
8

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-amine
  • 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
  • 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate
  • b-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
  • 2-chloroadenine
  • 2',3',5'-tri-O-benzoyl-2-chloroadenosine
  • 2-chloro-9-(3',5'-di-O-benzoyl-β-D-ribofuranosyl)-adenine
  • 9H-Purine, 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2,6-dichloro-
  • benzyl 2-acetamido 4,6-O-benzylidene-2-deoxy-3-O-mesyl-α-D-allopyranoside

DownStream

  • 2-chloroadenine
  • α-2d2F-Ara-1-P

Articles

The potential of clofarabine in MLL-rearranged infant acute lymphoblastic leukaemia.

Eur. J. Cancer 51 , 2008-21, (2015)

MLL-rearranged acute lymphoblastic leukaemia (ALL) in infants is the most difficult-to-treat type of childhood ALL, displaying a chemotherapy-resistant phenotype, and unique histone modifications, gen...

Preclinical examination of clofarabine in pediatric ependymoma: intratumoral concentrations insufficient to warrant further study.

Cancer Chemother. Pharmacol. 75 , 897-906, (2015)

Clofarabine, a deoxyadenosine analog, was an active anticancer drug in our in vitro high-throughput screening against mouse ependymoma neurospheres. To characterize the clofarabine disposition in mice...

Knockdown of Bcl-xL enhances growth-inhibiting and apoptosis-inducing effects of resveratrol and clofarabine in malignant mesothelioma H-2452 cells.

J. Korean Med. Sci. 29(11) , 1464-72, (2014)

Mcl-1 and Bcl-xL, key anti-apoptotic proteins of the Bcl-2 family, have attracted attention as important molecules in the cell survival and drug resistance. In this study, we investigated whether inhi...


More Articles

Related Compounds

  • CLOFARABINE TRIPHOSPHATE
  • 2-(1-{3-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]pentanamido}cyclopentyl)acetic acid
  • 3-{3-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]pentanamido}-2,2,3-trimethylbutanoic acid
  • 3-{2-[5-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pyridin-2-yl]acetamido}butanoic acid
  • 4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-oxobutanoic acid
  • 2-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanamido]-3,3,3-trifluoro-2-methylpropanoic acid
  • (2S)-2-[2-ethyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanamido]-3,3-dimethylbutanoic acid
  • 3-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5,5-dimethylhexanamido]-2-methylpropanoic acid
  • tert-butyl N-[3-(carbamothioylmethyl)-4-fluorophenyl]carbamate
  • 1-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylbutanoyl]azetidine-2-carboxylic acid
  • 4-[(4-ethyloxan-4-yl)carbamoyl]-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid