ChemicalBook > CAS DataBase List > N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester

N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester

Product Name
N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
CAS No.
918633-87-1
Chemical Name
N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
Synonyms
TH 302;CS-516;HAP-302;EOS-61724;EVOFOSFAMID;EvofosfaMide;TH-302, >=98%;TH 302; TH302;Evofosfamide(TH 302);TH-302 (Evofosfamide)
CBNumber
CB52604209
Molecular Formula
C9H16Br2N5O4P
Formula Weight
449.04
MOL File
918633-87-1.mol
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N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Property

Melting point:
97-98°C
Boiling point:
565.4±60.0 °C(Predicted)
Density 
1.97
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
0.34±0.70(Predicted)
form 
Solid
color 
Off-White to Pale Yellow
InChI
InChI=1S/C9H16Br2N5O4P/c1-15-8(6-12-9(15)16(17)18)7-20-21(19,13-4-2-10)14-5-3-11/h6H,2-5,7H2,1H3,(H2,13,14,19)
InChIKey
UGJWRPJDTDGERK-UHFFFAOYSA-N
SMILES
P(NCCBr)(NCCBr)(OCC1N(C)C([N+]([O-])=O)=NC=1)=O
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
22195
Product name
TH-302
Purity
≥95%
Packaging
1mg
Price
$40
Updated
2024/03/01
Cayman Chemical
Product number
22195
Product name
TH-302
Purity
≥95%
Packaging
5mg
Price
$168
Updated
2024/03/01
Cayman Chemical
Product number
22195
Product name
TH-302
Purity
≥95%
Packaging
10mg
Price
$276
Updated
2024/03/01
Cayman Chemical
Product number
22195
Product name
TH-302
Purity
≥95%
Packaging
25mg
Price
$590
Updated
2024/03/01
TRC
Product number
T338200
Product name
TH-302
Packaging
5mg
Price
$250
Updated
2021/12/16
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N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Chemical Properties,Usage,Production

Description

TH-302 is a hypoxia-activated prodrug and DNA alkylating agent with anticancer activity. It is selectively cytotoxic to H460 human non-small cell lung cancer (NSCLC) cells grown under hypoxic over normoxic conditions (IC50s = 0.019 and 5.1 μM, respectively). Under hypoxic conditions, TH-302 undergoes a one-electron reduction to form an active radical intermediate that is then further reduced to form a DNA-intercalating hydroxylamine. Under normoxic conditions, the radical intermediate is quenched and induces reformation of the inactive nitroazole prodrug. TH-302 reduces survival of H460 and HT-29 cells in a clonogenic assay (IC50s = 0.2 and 0.2 μM, respectively). In vivo, TH-302 (33 mg/kg per day) inhibits primary tumor growth by 41% in an MIA PaCa-2-RFP mouse orthotopic xenograft model. It inhibits tumor growth by greater than 40% in Calu-6 NSCLC, H82 small cell lung, A375 melanoma, PC-3 prostate, and BxPC-3 pancreatic cancer mouse xenograft models when administered at 50 mg/kg.

Uses

TH-302 is a 2-nitroimidazole triggered hypoxia-activated prodrug (HAP) of bromo-isophosphoramide mustard. Studies have shown that TH-302 treatment exhibited hypoxia-selective cytotoxicity and DNA damage in human cancer cell

in vivo

Evofosfamide (TH-302) is a hypoxia-activated prodrug known to activate selectively under the hypoxic conditions commonly found in solid tumors. The mean values of normalized Ktrans decrease 69.2% for Evofosfamide (TH-302)-treated mice in Hs766t tumors, decrease 46.1% for Mia PaCa-2 tumors and increase 4.9% in SU.86.86 tumors. Both changes for Hs766t and Mia PaCa-2 treatment groups are statistically significant (P<0.01) when compare to their own control group[2]. A significant reduction in the hypoxic fraction (HF) to 2.1%±4.7% is seen after 95% oxygen breathing (P<0.001), whereas 7% oxygen breathing significantly increase the HF to 29.5%±14.7% (P=0.029). Exposing rhabdomyosarcoma-bearing rats to increasing oxygen conditions abolish the effect of TH-302 and reduce the T4×SV from 20.4±3.5 to 15.3±2.5 days (P=0.007), whereas control animals have an increased T4×SV. Upon combination with radiotherapy, the T4×SV of TH-302-treated tumors decrease from 30.8±5.9 (Evofosfamide (TH-302)+radiotherapy) to 25.7±2.9 days (Evofosfamide (TH-302)+radiotherapy+95% O2)[3].

storage

Store at -20°C

References

[1] JIAN-XIN DUAN*. Potent and Highly Selective Hypoxia-Activated Achiral Phosphoramidate Mustards as Anticancer Drugs[J]. Journal of Medicinal Chemistry, 2008, 51 8: 2412-2420. DOI: 10.1021/jm701028q
[2] JESSICA D SUN. Selective tumor hypoxia targeting by hypoxia-activated prodrug TH-302 inhibits tumor growth in preclinical models of cancer.[J]. Clinical Cancer Research, 2012, 18 3: 758-770. DOI: 10.1158/1078-0432.ccr-11-1980

N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Suppliers

Canada 1 China 129 India 2 United States 12 Global 144
AdooQ BioScience, LLC
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+1 (866) 930-6790
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+1 (866) 333-9607
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info@adooq.com
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United States
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+1-800-259-7612
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TargetMol Chemicals Inc.
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+1-781-999-5354; +17819995354
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marketing@targetmol.com
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United States
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InvivoChem
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708-557-7486
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sales@invivochem.cn
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Cckinase, Inc.
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+1 (732)236-3202
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sales@cckinase.com
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BOC Sciences
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+1-631-485-4226
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inquiry@bocsci.com
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Aladdin Scientific
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TargetMol Chemicals Inc.
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support@targetmol.com
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Cayman Chemical Company
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Combi-Blocks Inc.
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NE Scientific
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View Lastest Price from N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester manufacturers

Career Henan Chemical Co
Product
N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester 918633-87-1
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2020-01-02

918633-87-1, N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl esterRelated Search:

N-Ethyl-3-methylaniline N-ethyl-pyrrolidone N-(2-Hydroxyethyl)-2-pyrrolidone TH287 TH588

  • N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
  • TH 302
  • EvofosfaMide
  • TH-302, >=98%
  • TH-302 (Evofosfamide)
  • (1-methyl-2-nitro-1H-imidazol-5-yl)methylN,N'-bis(2-bromoethyl)diamidophosphate
  • EOS-61724
  • Evofosfamide(TH 302)
  • EVOFOSFAMID
  • 2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine
  • (1-Methyl-2-nitro-1H-imidazol-5-yl)methyl N,N'-bis(2-bromoethyl)phosphorodiamidate
  • CS-516
  • TH 302; TH302
  • Phosphorodiamidic acid, N,N'-bis(2-bromoethyl)-, (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
  • HAP-302
  • Evofosfamide, 10 mM in DMSO
  • Phosphorodiamidic acid, N,N′-bis(2-bromoethyl)-, (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester (ACI)
  • Evofosfamide (TH-302) ，S2757
  • 918633-87-1
  • C9H16Br2N5O4P
  • TH-302
  • APIs
  • API