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Suramin sodium
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Name

Suramin sodium

 EINECS 204-949-3
CAS No. 129-46-4 Density N/A
PSA 551.01000 LogP 11.61040
Solubility >10mg/mL in water Melting Point N/A
Formula C51H34N6Na6O23S6 Boiling Point N/A
Molecular Weight 1429.19 Flash Point N/A
Transport Information N/A Appearance White crystalline powder
Safety 22-24/25 Risk Codes R22; R36/38
Molecular Structure Molecular Structure of 129-46-4 (Suramin sodium) Hazard Symbols Xn
Synonyms

1,3,5-Naphthalenetrisulfonicacid,8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-,hexasodium salt (9CI);1,3,5-Naphthalenetrisulfonic acid,8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-,hexasodium salt (8CI);8,8'-[Ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di(1,3,5-naphthalenetrisulfonicacid) hexasodium salt;Antrypol;BAY 205;Germanin;Germanin (pharmaceutical);Moranyl;Naganin;Naganine;Naphuride sodium;Suramin hexasodium;Suramin sodium;Suramine sodium;

Article Data 2

Suramin sodium Synthetic route

75-44-5

phosgene

8-(3-(3-aminobenzamide)-4-methylbenzamido)-naphthalene-1,3,5-trisulfonic acid trisodium salt

129-46-4

suramin sodium

Conditions
ConditionsYield
With sodium hydroxide In water; toluene Ambient temperature;
In water; toluene pH=4;

C10H7NO9S3(2-)*2Na(1+)

129-46-4

suramin sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 88.1 percent / toluene; H2O / pH 4
2: 95.6 percent / H2 / Pd/C / H2O
3: 68.8 percent / toluene; H2O / pH 4
4: 85.3 percent / H2 / Pd/C / H2O
5: toluene; H2O / pH 4
View Scheme

8-(3-amino-4-methylbenzamido)naphthalene-1,3,5-trisulfonic acid trisodium salt

129-46-4

suramin sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68.8 percent / toluene; H2O / pH 4
2: 85.3 percent / H2 / Pd/C / H2O
3: toluene; H2O / pH 4
View Scheme
Multi-step reaction with 3 steps
1: 2N NaOH / H2O; toluene / Ambient temperature
2: H2 / 10percent Pd/C / H2O / Ambient temperature
3: 2N NaOH / H2O; toluene / Ambient temperature
View Scheme

8-(4-methyl-3-nitrobenzamido)naphthalene-1,3,5-trisulfonic acid trisodium salt

129-46-4

suramin sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95.6 percent / H2 / Pd/C / H2O
2: 68.8 percent / toluene; H2O / pH 4
3: 85.3 percent / H2 / Pd/C / H2O
4: toluene; H2O / pH 4
View Scheme
Multi-step reaction with 4 steps
1: H2 / 10percent Pd/C / H2O / Ambient temperature
2: 2N NaOH / H2O; toluene / Ambient temperature
3: H2 / 10percent Pd/C / H2O / Ambient temperature
4: 2N NaOH / H2O; toluene / Ambient temperature
View Scheme

8-(4-methyl-3-(3-nitrobenzamido)benzamido)naphthalene-1,3,5-trisulfonic acid trisodium salt

129-46-4

suramin sodium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85.3 percent / H2 / Pd/C / H2O
2: toluene; H2O / pH 4
View Scheme
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / H2O / Ambient temperature
2: 2N NaOH / H2O; toluene / Ambient temperature
View Scheme
10397-30-5

4-methyl-3-nitrobenzoyl chloride

129-46-4

suramin sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 88.1 percent / toluene; H2O / pH 4
2: 95.6 percent / H2 / Pd/C / H2O
3: 68.8 percent / toluene; H2O / pH 4
4: 85.3 percent / H2 / Pd/C / H2O
5: toluene; H2O / pH 4
View Scheme
Multi-step reaction with 5 steps
1: 2N NaOH / H2O; toluene / Ambient temperature
2: H2 / 10percent Pd/C / H2O / Ambient temperature
3: 2N NaOH / H2O; toluene / Ambient temperature
4: H2 / 10percent Pd/C / H2O / Ambient temperature
5: 2N NaOH / H2O; toluene / Ambient temperature
View Scheme

8-amino-1,3,5-naphthalenetrisulfonic acid trisodium salt

129-46-4

suramin sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 2N NaOH / H2O; toluene / Ambient temperature
2: H2 / 10percent Pd/C / H2O / Ambient temperature
3: 2N NaOH / H2O; toluene / Ambient temperature
4: H2 / 10percent Pd/C / H2O / Ambient temperature
5: 2N NaOH / H2O; toluene / Ambient temperature
View Scheme
30516-87-1

3'-azido-2',3'-deoxythymidine

129-46-4

suramin sodium

C61H46N11O26S6(5-)*5Na(1+)

Conditions
ConditionsYield
With phosphorus pentaoxide In N,N-dimethyl-formamide at 20℃;42%
129-46-4

suramin sodium

25526-93-6

alovudine

C61H46FN8O26S6(5-)*5Na(1+)

Conditions
ConditionsYield
With phosphorus pentaoxide In N,N-dimethyl-formamide at 20℃;40%
129-46-4

suramin sodium

8-(3-(3-aminobenzamide)-4-methylbenzamido)-naphthalene-1,3,5-trisulfonic acid trisodium salt

Conditions
ConditionsYield
With water at 90℃; for 144h; Product distribution; Rate constant; Thermodynamic data; pH 7, var. temp., Ea;

Suramin sodium Specification

The Suramin sodium with the cas number 129-46-4 is also called 1,3,5-Naphthalenetrisulfonicacid,8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-,sodium salt (1:6). Both the systematic name and IUPAC name are hexasodium 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonatonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]
carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonate. Its EINECS registry number is 204-949-3. This chemical belongs to the following product categories: (1)Active Pharmaceutical Ingredients; (2)Purinergics P2 receptor. It should be stored at 0-6°C.

The properties of the chemical are: (1)ACD/LogP: 2.19; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -6.3; (4)ACD/LogD (pH 7.4): -6.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 29; (10)#H bond donors: 12; (11)#Freely Rotating Bonds: 16; (12)Polar Surface Area: 481.29 Å2.

Biological Activity: (1)Non-selective P2 purinergic antagonist; (2)Also blocks calmodulin binding to recognition sites and G protein coupling to G protein-coupled receptors; (3)Anticancer and antiviral agent.

You can still convert the following datas into molecular structure:
(1)SMILES: [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O=C(Nc1cc(ccc1C)C(=O)Nc3c2c(cc(cc2c(cc3)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O)c8cccc(NC(=O)Nc7cc(C(=O)Nc6cc(C(=O)Nc5c4c(cc(cc4c(cc5)S([O-])(=O)=O)S([O-])(=O)=O) S([O-])(=O)=O)ccc6C)ccc7)c8
(2)InChI: InChI=1/C51H40N6O23S6.6Na/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80;;;;;;/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80);;;;;;/q;6*+1/p-6
(3)InChIKey: VAPNKLKDKUDFHK-CYFPFDDLAT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   Biochemical and Biophysical Research Communications. Vol. 136, Pg. 64, 1986.
 
mouse LD50 intravenous 620mg/kg (620mg/kg)   "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 1423, 1989.

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