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53910-25-1

53910-25-1 structure
53910-25-1 structure
Name pentostatin
Synonyms Nipent
DCF
yk-176
(R)-3-(2-Deoxy-b-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
Imidazo(4,5-d)(1,3)diazepin-8-ol, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydro-, (R)-
Imidazo[4,5-d][1,3]diazepin-8-ol, 3- (2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydro-, (R)-
(8R)-3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
Imidazo[4,5-d][1,3]diazepin-8-ol, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydro-, (R)-
deoxycoformycin
2'-deoxy-D-coformycin
Pentostatin
2'-deoxycoformycin
(R)-3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo(4,5-d)(1,3)diazepin-8-ol
Cl 825
CO-Vidarabine
Co-V
ci-825
Imidazo[4,5-d][1,3]diazepin-8-ol, 3- (2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8- tetrahydro-, (R)-
(8R)-3-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
Imidazo[4,5-d][1,3]diazepin-8-ol, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydro-, (8R)-
PD-ADI
Imidazo(4,5-d)(1,3)diazepin-8-ol, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydro-, (R)-
(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-3,6,7,8-tétrahydroimidazo[4,5-d][1,3]diazépin-8-ol
Coforin
Description Pentostatin is an irreversible inhibitor of adenosine deaminase with Ki of 2.5 pM.
Related Catalog
Target

Ki: 2.5 pM (adenosine deaminase)

In Vivo In ECP and Pentostatin (4 mg/m2, i.v.) treatment, all dogs develop granulocytopenia with <500 granulocytes/μL from day 4. Thrombocytopenia (<20,000 platelets/μL) occurs from day 7 after HCT with nadirs of 3000 to 14000 platelets/μL[1]. Pentostatin (2 mg/kg) in combination with cordycepin (2 mg/kg) is 100% effective in the T. evansi-infected mice. There is an increase in levels of some biochemical parameters, especially on liver enzymes, which are accompanied by histological lesions in the liver and kidneys. Pentostatin individually has no curative effect on infected groups[2].
Animal Admin All recipient dogs are conditioned for transplantation by 920 cGy TBI at 7 cGy/minute using a linear accelerator. Dogs in group A1receive ECP administered on days −2 and −1 with TBI on day 0 and dogs in group A2receive ECP on days −6 and −5, intravenous (IV) infusion of pentostatin at a dose of 4 mg/m2 on days −4 and −3, and TBI on day 0. Donor marrow cells from DLA-nonidentical donors are aspirated under general anesthesia through needles inserted into humeri and femora and stored in heparinized tissue culture medium at 4°C for no more than 6 hours. Within 4 hours of TBI, harvested marrow cells are infused IV into recipients at a median dose of 2.9 (range, 1.9 to 6.1) ×108 total nucleated cells (TNC)/kg. The day of marrow grafting is designated as day 0. In addition to marrow graft, recipients are given IV infusions of peripheral blood buffy coat cells obtained by leukapheresis from the marrow donor on days 1 and 2, at a median dose of 2.3 (range, 1.2 to 6.9) ×108 TNC/kg to ensure consistent hematopoietic engraftment. MTX, at a dose of 0.4 mg/kg intravenously is used as postgrafting immunosuppression and administered on days +1, +3, +6 and +11, then weekly thereafter until day 102.
References

[1]. Bethge WA, et al. Extracorporeal photopheresis combined with pentostatin in the conditioning regimen for canine hematopoietic cell transplantation does not prevent GVHD. Bone Marrow Transplant. 2014 Sep;49(9):1198-204.

[2]. Dalla Rosa L, et al. Cordycepin (3'-deoxyadenosine) pentostatin (deoxycoformycin) combination treatment of mice experimentally infected with Trypanosoma evansi. Parasitology. 2013 Apr;140(5):663-71.
Density 1.8±0.1 g/cm3
Boiling Point 673.1±65.0 °C at 760 mmHg
Melting Point 220-225ºC
Molecular Formula C11H16N4O4
Molecular Weight 268.269
Flash Point 360.9±34.3 °C
Exact Mass 268.117157
PSA 112.13000
LogP -2.16
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.793
Storage condition -20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NI2931000
CHEMICAL NAME :
Imidazo(4,5-d)(1,3)diazepin-8-ol, 3-(2-deoxy-beta-D-pentofuranosyl)-3,6,7,8-tetrahydro- , (R)-
CAS REGISTRY NUMBER :
53910-25-1
LAST UPDATED :
199703
DATA ITEMS CITED :
23
MOLECULAR FORMULA :
C11-H16-N4-O4
MOLECULAR WEIGHT :
268.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
390 mg/kg/3D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - thrombocytopenia Blood - other hemolysis with or without anemia
REFERENCE :
IEDIEP Internal Medicine. (The Japanese Society of Internal Medicine, 34-3, 3-chome, Hongo, Bunkyo-ku, Tokyo 113, Japan) V.31- 1992- Volume(issue)/page/year: 34,593,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
227 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - hematuria Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 24,7888,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
122 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB84-211424
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
360 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Gastrointestinal - changes in structure or function of salivary glands Gastrointestinal - nausea or vomiting
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 24,7888,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
650 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Endocrine - other changes Blood - changes in bone marrow (not otherwise specified)
REFERENCE :
TOPADD Toxicologic Pathology. (c/o Dr. F.A. de la Iglesia, Warner-Lambert Co., Pharmaceutical Research Div., POB 1047, Ann Arbor, MI 48106) V.6(3/4)- 1978- Volume(issue)/page/year: 22,519,1994
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/kg/4W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - changes in lung weight Endocrine - changes in spleen weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
CCPHDZ Cancer Chemotherapy and Pharmacology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1978- Volume(issue)/page/year: 5,83,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
18200 ug/kg/26W-C
TOXIC EFFECTS :
Blood - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,4277,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
28 mg/kg/4W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,1271,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
91 ug/kg/26W-C
TOXIC EFFECTS :
Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,4277,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
14 mg/kg/4W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - other changes in urine composition Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,1271,1991 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
7500 ug/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 44,325,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
7500 ug/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - sex ratio
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 44,325,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 ug/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow) Reproductive - Specific Developmental Abnormalities - immune and reticuloendothelial system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 25(2),36A,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 40,615,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 45,91,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 47,17,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 47,17,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
5 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,3977,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
8300 ug/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,3965,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
8300 ug/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,3965,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
28 ug/kg
SEX/DURATION :
female 15-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,4329,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
28 ug/kg
SEX/DURATION :
female 15-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,4329,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
1300 ug/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Fertility - abortion Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 25,4319,1991
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Hazard Codes Xn
Risk Phrases 22
RIDADR UN 2811 6.1 / PGIII
HS Code 2934999090
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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