Carisoprodol

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Cat Number

API0232179

CAS Number

78-44-4

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Product Detail Description Scientific Support Customer Q&A

CAS Number

78-44-4

EINECS

201-118-7

Storage

Store at room temperature

Synonyms

Isomeprobamate; Carisoprodate; Carisoprodatum; Carisoma; Isobamate; Isoprothane; Flexartal; Isoprotane; Miolisodal; Atonalyt; Isopropyl meprobamate

Molecular Formula

C12H24N2O4

Molecular Weight

260.33

Smiles

CCCC(C)(COC(=O)N)COC(=O)NC(C)C

Appearance

White Solid

Melting Point

92-92°C

Boiling Point

403.59°C (Estimate)

Relative Density

1.1035 (Estimate)

General Description

Carisoprodol is a centrally acting skeletal muscle relaxant that is a carbamate derivative of meprobamate, containing two carbamate groups. Its structure is 2-methyl-2-propyl-1,3-propanediol dicarbamate. Carisoprodol is a white crystalline powder with a characteristic odor. It is a prodrug that is metabolized to meprobamate, which contributes to its pharmacological effects.

Mechanism of Action

Carisoprodol acts centrally in the brainstem and spinal cord, producing its muscle relaxant effects through a combination of actions, including the modulation of GABA-A receptors and the inhibition of polysynaptic reflexes. The drug does not directly affect the neuromuscular junction. Its sedative properties are primarily due to the parent compound, while the metabolite meprobamate contributes to its anxiolytic and muscle-relaxant effects.

Application

Carisoprodol is indicated as an adjunct to rest, physical therapy, and other measures for the relief of acute, painful musculoskeletal conditions, such as muscle spasms and strains. It is particularly effective in acute low back pain.

Carisoprodol directly gated and allosterically potentiated both synaptic (αxβzγ2) and extrasynaptic (αxβzδ) GABAA receptors in HEK293 cells. β1 subunits conferred highest direct gating efficacy and β2 subunits conferred highest allosteric modulation. α1 subunits were most responsive to allosteric enhancement, while α3 subunits showed reduced direct gating. In extrasynaptic receptors, carisoprodol was more efficacious than GABA as a direct agonist. Direct gating and inhibition were voltage-insensitive, but allosteric modulation was voltage-dependent.

Fig. 1 Voltage-dependent effect of carisoprodol actions on GABAA receptors. (Kumar M, et al., 2015)

References

Kumar M, et al. Assessment of subunit-dependent direct gating and allosteric modulatory effects of carisoprodol at GABA(A) receptors. Neuropharmacology. 2015;97:414-425.

Does Carisoprodol require protection from moisture during long-term storage?

Yes, it is slightly hygroscopic and can hydrolyze to meprobamate in the presence of moisture. Store in tightly sealed containers with desiccant.

What is the recommended storage temperature for Carisoprodol?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which accelerate ester hydrolysis and degradation.

Is Carisoprodol stable in tablet formulations with standard excipients?

Yes, when formulated with moisture-protective packaging.

How is the impurity meprobamate (a hydrolysis product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.