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Home> Encyclopedia >Immune Function Agents>Pharmaceutical Intermediates>Pharmaceutical
Aztreonam structure
Aztreonam structure


Iupac Name:2-[(E)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid
CAS No.: 78110-38-0
Molecular Weight:435.426
Modify Date.: 2022-11-07 21:27
Introduction: Aztreonam is the first member of the monobactam class of antibiotics to beintroduced into the world market. It possesses high β-lactamase stability andmoderately good activity against gram negative aerobes such as E. coli, S. marcescens,-9 Proteus Providencia, Salmonella, g. influenzae, E. gonorrhea, and &. pneumonia.While somewhat less potent against Pseudomonas aeruginosa, it is nonetheless oneof the better β-lactams against this species. It has poor activity against grampositive organisms. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(2s-(2-alpha,3-beta(z)))-dinyl)amino)-2-oxoethylidene)amino)oxy)-2-methyl (2S,3S)-3-{[(2Z)-2-(2-Ammonio-1,3-thiazol-4-yl)-2-{[(2-carboxy-2-propanyl)oxy]imino}acetyl]amino}-2-methyl-4-oxo-1-azetidinesulfonate (2S,3S)-3-{[(2Z)-2-(2-Ammonio-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate (E)-2-(((1-(2-aminothiazol-4-yl)-2-((2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid [2S-[2a,3b(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic Acid 2-({[(1Z)-1-(2-Amino-1,3-thiazol-4-yl)-2-{[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino}-2-oxoethylidene]amino}oxy)-2-methylpropanoic acid Azactam Azonam Azteronam Azthreonam Aztreon Aztreonam and Sodium Carbonate Aztreonam for injection Aztreonam L-Arginine Aztreonam(β-form) Aztreonam/arginine CAYSTON EINECS 278-839-9 MFCD00072145 monobactam Nebactam Primbactam Propanoic acid, 2-[[[(1Z)-1-(2-amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methyl- SQ 26,776 sq26,776

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1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C13H17N5O8S2 (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Refractive index
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Appearance
white to off-white crystals
2.2 Storage
Store at -20°C.
2.3 Color/Form
white to beige
2.4 pKa
pKa -0.7(H2O t=RT Iunde?ned) (Uncertain);2.75(H3O t=RT Iunde?ned) (Uncertain);3.91(H4O t=RT Iunde?ned) (Uncertain)
2.5 Water Solubility
Soluble in DMF/water (1:1) at 50 mg/ml
2.6 StorageTemp
room temp
3. Use and Manufacturing
3.1 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 2 of 3 companies. For more detailed information, please visit ECHA C&L website

Of the 1 notification(s) provided by 1 of 3 companies with hazard statement code(s):

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501
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3.2 Usage
It is Mainly used for the infections caused by sensitive gram-negative bacteria , including pneumonia, pleurisy, abdominal infections, biliary tract infections, bone and joint infections, skin and soft tissue inflammation, especially for urinary tract infections, but also for sepsis. Because this product has good resistance to enzyme performance, therefore, when a microorganism is not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs ,the product should often be effective.
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
NONH for all modes of transport
4.1 Safety Profile
Moderately toxic by severalroutes. An experimental teratogen. Other experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx and SOx.
4.2 WGK Germany
4.2 Safety

Moderately toxic by several routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and SOx.
Hazard Codes??HarmfulXn
Risk Statements? 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements? 22-24/25-36-26
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
WGK Germany: 2
RTECS: UA2451400

4.3 Specification

The main role?of Aztreonam?(CAS NO.78110-38-0) is used to treat infections which?caused by sensitive gram-negative bacteria .?Aztreonam (CAS NO.78110-38-0) is a toxic material, burning will produce toxic fumes of nitrogen oxides and sulfur oxides, Besides should be stored and transported in low-temperature, drying environment. separately with oxidizing agents. Fire extinguishing agents water, carbon dioxide, dry powder, foam would be used if emergency.

4.4 Toxicity
1. ???

ivn-rat TDLo:1100?mg/kg (7-17?D preg):TER

??? NKRZAZ ?? Chemotherapy (Tokyo). 33 (Suppl 1)(1985),203.
2. ???

ipr-rat LD50:2549?mg/kg

??? NKRZAZ ?? Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
3. ???

scu-rat LD50:3154?mg/kg

??? NKRZAZ ?? Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
4. ???

ivn-rat LD50:2001?mg/kg

??? KSRNAM ?? Kiso to Rinsho. Clinical Report. 19 (1985),468.
5. ???

ipr-mus LD50:2897?mg/kg

??? NKRZAZ ?? Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
6. ???

scu-mus LD50:3906?mg/kg

??? NKRZAZ ?? Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
7. ???

ivn-mus LD50:1963?mg/kg

??? NKRZAZ ?? Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
View all

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)


Precautionary statement(s)








2.3 Other hazards which do not result in classification


8. Other Information
8.0 Description
Aztreonam is the first member of the monobactam class of antibiotics to be introduced into the world market. It possesses high β-lactamase stability and moderately good activity against gram negative aerobes such as E. coli, S. marcescens, -9 Proteus Providencia, Salmonella, g. influenzae, E. gonorrhea, and &. pneumonia. While somewhat less potent against Pseudomonas aeruginosa, it is nonetheless one of the better β-lactams against this species. It has poor activity against gram positive organisms.
8.1 Originator
Squibb (USA)
8.2 Manufacturing Process
This mixture was sterilized for 15 minutes at 121°C at 15 lbs/inch2 steam pressure prior to use. The fermentation flasks were incubated at 25°C for 40 to 45 hours on a of rotary shaker. A 250 liter batch of Agrobacterium radiobacter A.T.C.C. No. 31700 is fermented in a 100 gallon steel vessel with a media and operating conditions described below. Culture of Agrobacterium radiobacter grown out on agar slants, pH 7.3 consisted of yeast extract (1 g), beef extract (1 g), NZ amine A (2 g), glucose (10 g), agar (15 g) in 1000 ml distilled water. Loopful of surface growth from agar slant was used as the source of incolumn. Medium of oatmeal (20 g), tomato paste (20 g) tapped water to 1000 ml, pH 7, was sterilized for 15 min at 121°C at 15 lbs/inch2 steam pressure prior to use. 100 ml of the medium, containing incolumn is incubated at 25°C for about 24 hours on a rotary shaker. It was added to a mixture of yeast extract (5 g), glucose (10 g) in 1 L distilled water and incubated for about 42 hours at 25°C in 100 gallon stainless steel fermentation vessel.
During incubation, the broth is agitated at 155 r.p.m. and aerated at rate of 10.0 cubic feet per minute. An antifoam agent (Ucon LB625, Union Carbide) was added as needed. The fermentation beer was adjusted to pH 4 with aqueous HCl and calls separated by centrifugation. The supernatante (200 L) was extracted with 40 L of 0.05 m cetyldimethylbenzyl ammonium chloride in dichloromethane and extract concentrated in vacuo to 5.5 L. The concentrate was then extracted with solution of 177 g of sodium thiocyanate in 2 L of water, adjusting the mixture of pH 4.35 with phosphoric acid. The aqueous extract was concentrated in vacuo to 465 ml and added to 1840 ml of methanol. Solids are filtrated yielded 194 g of crude solid product. It was dissolved and chromatographed on a 5x106.5 cm column of Sephadex G-10 three times and after concentrating in vacuo gave 3.5 g of crude antibiotic M53 (azetreonam) which was chromatographed at first on QAE Sephadex A- 25 (liner gradient, prepared from 2.5 L of water and 2.5 L of 0.25 M sodium nitrate). Then the residue (fractions 26-75) gave M53 (natrium salt) after evaporation. It was triturated with methanol and the souble fraction, 0.40 g was chromatographed on a 2.5x20 cm column of Diaion HP20AG, eluting at 2 ml per minute with water and collecting 20 ml fractions. Fractions 26-75 gave 51.9 mg of antibiotic M53 (sodium salt).
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8.3 Brand name
Azactam (Bristol-Myers Squibb);PRIMBACTAM.
8.4 Therapeutic Function
8.5 Antimicrobial activity
Concentrations (mg/L) inhibiting 50% of other organisms are: Aeromonas spp., 0.1;Acinetobacter spp., 16; Mor. catarrhalis, 0.1; Burkholderia cepacia, 2; and Yersinia spp., 0.1. Synergy has been shown with gentamicin, tobramycin and amikacin against 52–89% of strains of Ps. aeruginosa and gentamicin-resistant Gram-negative bacteria.
8.6 General Description
Azactam (aztreonam for injection, intravenous or intramascular)contains the active ingredient aztreonam, which is amember of the monobactam class of antibiotics. A true antibiotic,aztreonam was originally isolated from cultures ofthe bacterium Chromobacterium violaceum. Now, the antibioticis prepared by total synthesis. Monobactams possessa unique monocyclic β-lactam nucleus, and are structurallyunlike other β-lactams like the penicillins, cephalosporins,carbapenems, and cephamycins. The β-lactam arrangementof aztreonam is unique, possessing an N-sulfonic acid functionality.This group activates the β-lactam ring towardattack. The side chain (3-position) aminothiazolyl oximemoiety and the 4-methyl group specify the antibacterialspectrum and β-lactamase resistance.
The mechanism of action of aztreonam is essentially identicalto that of other β-lactam antibiotics. The action of aztreonamis inhibition of cell wall biosynthesis resulting from ahigh affinity of the antibiotic for penicillin binding protein 3(PBP-3). Unlike other β-lactam antibiotics, aztreonam doesnot induce bacterial synthesis of β-lactamases. The structureof aztreonam confers resistance to hydrolysis by penicillinasesand cephalosporinases synthesized by most Gramnegativeand Gram-positive pathogens. Because of theseproperties, aztreonam is typically active against Gram-negativeaerobic microorganisms that resist antibiotics hydrolyzedby -lactamases. Aztreonam is active against strains that aremultiply-resistant to antibiotics such as cephalosporins, penicillins,and aminoglycosides. The antibacterial activity ismaintained over a broad pH range (6–8) in vitro, as well as inthe presence of human serum and under anaerobic conditions.
Aztreonam for injection is indicated for the treatment ofinfections caused by susceptible Gram-negative microorganism,such as urinary tract infections (complicated and uncomplicated),including pyelonephritis and cystitis(initial and recurrent) caused by E. coli, K. pneumoniae, P.mirabilis, P. aeruginosa, E. cloacae, K. oxytoca, Citrobactersp., and S. marcescens. Aztreonam is also indicated for lowerrespiratory tract infections, including pneumonia and bronchitiscaused by E. coli, K. pneumoniae, P. aeruginosa, H.influenzae, P. mirabilis, S. marcescens, and Enterobacterspecies. Aztreonam is also indicated for septicemia causedby E. coli, K. pneumoniae, P. aeruginosa, P. mirabilis, S.marcescens, and Enterobacter spp. Other infections respondingto aztreonam include skin and skin structure infections,including those associated with postoperative wounds andulcers and burns. These may be caused by E. coli, P.mirabilis, S. marcescens, Enterobacter species, P. aeruginosa,K. pneumoniae, and Citrobacter species. Intra-abdominalinfections, including peritonitis caused by E. coli,Klebsiella species including K. pneumoniae, Enterobacterspecies including E. cloacae, P. aeruginosa, Citrobacterspecies including C. freundii, and Serratia species includingS. marcescens. Some gynecologic infections, including endometritisand pelvic cellulitis caused by E. coli, K. pneumoniae,Enterobacter species including E. cloacae, and P.mirabilis also respond to aztreonam.
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8.7 Biochem/physiol Actions
Aztreonam is a monobactam antibiotic used primarily to treat gram-negative bacterial infections. It is an older compound being re-examined as a therapeutic agent because of increasing carbapenem resistance in aerobic Gram-negative bacilli and because aztreonam is stable to Ambler class B metallo-β-lactamases. It is used alone or more commonly in combination with β-lactamase inhibitors such as avibactim.
8.8 Pharmacokinetics
Cmax 1 g intravenous: 90 mg/L end infusion
1 g intramuscular: 46 mg/L after 1 h
Plasma half-life: 1.7 h
Volume of distribution: 0.18 L/kg
Plasma protein binding: 56%
Absorption and distribution
Oral bioavailability is less than 1%. Peak concentrations above the median MIC for most Gram-negative pathogens are achieved in most tissues and body fluids after 1 g intramuscular or intravenous doses.
Metabolism and excretion
It is not extensively metabolized, the most prominent product, resulting from opening the β-lactam ring, being scarcely detectable in the serum and accounting for about 6% of the dose in the urine and 3% in the feces.
It is predominantly eliminated in the urine, where 58–72% appears within 8 h. Less than 12% is eliminated unchanged in the feces, suggesting low biliary excretion.
8.9 Usage
Aztreonam is used to treat severe infections of the urinary tract, lower respiratory tract, skin, stomach, female reproductive organs, and other body systems.
8.10 Clinical Use
Urinary tract infections, including pyelonephritis and cystitis
Lower respiratory tract infections, including pneumonia and bronchitis
caused by Gram-negative bacilli
Skin and skin structure infections, including postoperative wounds, ulcers
and burns
Intra-abdominal infections, including peritonitis
Gynecological infections, including endometritis and pelvic cellulitis
8.11 Side effects
Local reactions occasionally occur at the injection site. Systemic reactions include diarrhea, nausea and/or vomiting and rash (1–1.3%). Neutropenia was seen in 11.3% of the pediatric patients younger than 2 years. Pseudomembranous colitis has been reported.
There are no reactions in patients with immunoglobulin E (IgE) antibodies to benzylpenicillin or penicillin moieties. It is rarely cross-reactive with other β-lactam antibiotics and is weakly immunogenic.
8.12 Safety Profile
Moderately toxic by severalroutes. An experimental teratogen. Other experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx and SOx.
8.13 Chemical Synthesis
Aztreonam, (Z)-2[[[(2-amino-4-thiazolyl)[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]cabamoyl]methylen]amino]oxy]-2-methylpropionoic acid (, is synthesized from tert-butyloxycarbonylthreonine, which is reacted with O-benzylhydroxylamine in the presence of dicyclohexylcarbodimide and 1-hydroxybenzotriazole, to form the benzyl hydroxamide derivative ( This product undergoes a reaction with triphenylphosphine and ethyl azodicarboxylate, which results in the cyclodehydration of the product to (3S-trans)-N-benzyloxy-3-tert-butyloxycarbonylamino-4-methyl-azetidinone ( Debenzylating this by hydrogen reduction using a palladium on carbon catalyst forms (3S-trans)-N-hydroxy-3-tertbutyloxycarbonyl-amino-4-methyl-azetidinone ( The hydroxyl group in this compound is removed by reducing it with titanium trichloride, which forms azetidinone ( Removing the tert-butyloxycarbonyl protection using trifluoroacetic acid and subsequent acylation of the resulting product with the benzyl chloroformate gives (3S-trans)-benzyloxycarbonylamino-4-methylazetidinone ( Sulfonating this product with a mixture of sulfur trioxide and dimethylformamide gives the corresponding N-sulfonic acid. Turning the resulting Nsulfonic acid into a potassium salt by reacting it with potassium hydrophosphate, followed by replacing the potassium cation with a tetrabutylammonium cation by reacting it with tetrabutylammonium sulfate gives the product ( Reducing this with hydrogen using a palladium on carbon catalyst gives 3-amino-4-methyl-monobactamic acid ( Acylating this with (Z) 2-amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]imino] 4-thiazoleacetic acid in the presence of dicyclohexylcarbodiimide and 1-hydroxy-benzotriazole gives the diphenylmethyl ester of the desired aztreonam (, which is hydrolyzed to aztreonam ( using trifluoroacetic acid.

It is believed that the methyl group at position 4 increases the stability of the beta-lactam ring with respect to most beta-lactamases, and at the same time it does not induce formation of beta-lactamase as cephalosporins and imipenems do.
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8.14 Veterinary Drugs and Treatments
Aztreonam is a monobactam antibiotic that may be considered for use in small animals for treating serious infections caused by a wide variety of aerobic and facultative gram-negative bacteria, including strains of Citrobacter, Enterobacter, E. coli, Klebsiella, Proteus, Pseudomonas and Serratia. The drug exhibits good penetration into most tissues and low toxic potential and may be of benefit in treating infections when an aminoglycoside or a fluoroquinolone are either ineffective or are relatively contraindicated. Any consideration for using aztreonam must be tempered with the knowledge that little clinical experience or research findings have been published with regard to target species.
Aztreonam has also been used to treat pet fish (koi) infected with Aeromonas salmonocida.
8.15 Merck
8.16 indications
It is mainly used for the treatment of infections caused by susceptible strains which include the respiratory system, urinary, reproductive system infections (including acute gonorrhea), intra-abdominal infections, skin and soft tissue infections, before surgery preventing infections, other serious infections, such as sepsis.
8.17 Chemical properties
white or colorless powder crystals, melting at 227 ℃ (decomposition). It is dissolved in dimethyl formamide, slightly soluble in methanol, very slightly soluble in ethanol, insoluble in toluene, chloroform or ethyl acetate.
Aztreonam disodium: C13 H15N5Na2O8 . Acute toxicity LD50 (mg/kg): 3300 intravenous injection in mice, 6600 in rats intraperitoneally.
8.18 Uses
It is Mainly used for the infections caused by sensitive gram-negative bacteria , including pneumonia, pleurisy, abdominal infections, biliary tract infections, bone and joint infections, skin and soft tissue inflammation, especially for urinary tract infections, but also for sepsis. Because this product has good resistance to enzyme performance, therefore, when a microorganism is not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs ,the product should often be effective.
8.19 Category
Toxic substances
8.20 Toxicity grading
Middle toxic
8.21 Acute toxicity
Intraperitoneal-rat LD50: 2549 mg/kg; intraperitoneal-Mouse LD50: 2897 mg/kg.
8.22 Flammability and hazard characteristics
Combustible; combustion produces toxic fumes of nitrogen oxides and sulfur oxides.
8.23 Storage Characteristics
Ventilated, low-temperature ,dry storeroom.
8.24 Extinguishing agent
Dry powder, foam, sand, carbon dioxide, water spray.
8.25 Chemical Properties
White Crystalline Powder
8.26 Uses
The first totally synthetic monocyclic β-lactam antibiotic.
8.27 Uses
8.28 Uses
The first totally synthetic monocyclic ?lactam antibiotic
8.29 Brand name
Azactam (Bristol-Myers Squibb).
9. Computational chemical data
  • Molecular Weight: 435.426g/mol
  • Molecular Formula: C13H17N5O8S2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.3
  • Exact Mass: 435.05185486
  • Monoisotopic Mass: 435.05185486
  • Complexity: 808
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 12
  • Topological Polar Surface Area: 238
  • Heavy Atom Count: 28
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
10. Question & Answer
  • In our daily lives, we often encounter various diseases and symptoms. Doctors often prescribe different drugs to treat different diseases, including Aztreonam. Aztreonam, also known as Aztreonam, is a..
  • Aztreonam is used to treat urinary tract infections, lower respiratory tract infections, sepsis, intra-abdominal infections, gynecological infections, and skin and soft tissue infections caused by sus..
  • Aztreonam is an injectable drug that has a very good effect on inhibiting most gram-negative bacteria. Therefore, the drug mechanism of Aztreonam is also very good. Of course, it can also be used as a..
  • Aztreonam is an antibiotic medication that has proven to be effective in treating various infections caused by different types of bacteria. It is commonly used in clinical settings due to its remarkab..
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