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Purity: ≥98%
Chlorphenesin (NSC-6401) is a synthetic preservative and cosmetic biocide that helps prevent the growth of microorganisms. It is used in skin care as a cosmetic biocide, and acts as a centrally acting muscle relaxant. Also acts as a reversible antigen-associated immunosuppressant, and an antibacterial and antifungal agent used in numerous eye care cosmetics.
| Targets |
The drug acts as an antigen-associated immunosuppressant.
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|---|---|
| ln Vitro |
Human meibomian gland epithelial cells (HMGECs) exposed to chlorphenesin (0.01, 0.1, 0.3%; 30-min exposure) exhibit a dose-dependent significant reduction in Akt pathway activity[2].
The effects of chlorphenesin (0.1, 0.3%; 24 hours) include rounding, atrophy, poor adherence, detachment, and a marked decrease in the number of immortalized HMGECs (IHMGECs)[2]. Inhibition of IgE-mediated histamine release from human leukocytes is mentioned as a known effect .[1] Hemagglutination-inhibition tests show that Chlorphenesin does not alter antigenic determinants, as antigen-antibody neutralization occurs in the presence or absence of the drug.[1] |
| ln Vivo |
Chlorphenesin suppresses antibody response in rabbits when co-administered with specific bacterial antigens after pre-incubation.
At 10 mg/ml, it completely inhibits antibody production against the common antigen of gram-positive bacteria (CA+). At 1 mg/ml, it substantially suppresses antibody response (titer 20 vs. control 320).[1] The immunosuppressive effect is reversible: cooling the antigen-drug mixture to 4°C precipitates the drug and restores immunogenicity.[1] Rabbits immunized with antigen-drug mixtures are immunologically primed, showing a boosted antibody response upon subsequent antigen challenge.[1] The drug does not suppress antibody response to purified lipopolysaccharide of E. coli O113 or O antigen from E. coli O111 culture supernatant.[1] |
| Animal Protocol |
Albino rabbits (2–3 kg) were immunized via intravenous injection with 1 ml of antigen alone or antigen-drug mixture.
Three injections were given at 3–4 day intervals.[1] Chlorphenesin was dissolved in phosphate hemagglutination buffer (pH 7.3) at 10 mg/ml and heated at 56°C for 30 minutes before use.[1] For immunosuppression studies, antigen and drug were mixed at a ratio of 1:9 (antigen: drug solution) and incubated at 37°C for 30 minutes prior to injection.[1] Control groups received non-incubated mixtures, separately injected drug and antigen, or antigen with buffer.[1] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Rapid and complete. Metabolism/Metabolites: Hepatic metabolism. 85% of the dose is excreted within 24 hours as glucuronide metabolites. Biological Half-Life: 2.3–5 hours. |
| Toxicity/Toxicokinetics |
Chlorphenesin has hemolytic effects at concentrations above 1 mg/ml. [1]
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| References | |
| Additional Infomation |
Chlorphenesin is a glycerol derivative in which a hydrogen atom on one of the primary hydroxyl groups is replaced by a 4-chlorophenyl group. It possesses antifungal and antimicrobial properties and is used to treat skin and vaginal infections. Its 1-carbamate ester can be used as a skeletal muscle relaxant to treat painful muscle spasms. It has a dual action as a muscle relaxant, antimicrobial agent, and antifungal agent. It is a diol compound belonging to the propane-1,2-diol and monochlorobenzene classes. A centrally acting muscle relaxant. Its mechanism of action is not fully understood. (Excerpt from Martindale Pharmacopoeia, 30th edition, p. 1203) See also: ... See more ...
Drug Indications Used in conjunction with rest and physical therapy for the treatment of injuries and other painful muscle disorders. Chlorphenesin has been used to treat trigeminal neuralgia (a neurological disorder characterized by severe facial pain). It has also been investigated as a regulator of histamine release. Mechanism of Action The mechanism of action of chlorphenesin is not well understood, and its efficacy is primarily assessed through subjective response. Chlorphenesin is known to act on the central nervous system (CNS) rather than directly on skeletal muscle. Pharmacodynamics Clorphenesin is a muscle relaxant. It blocks the transmission of nerve impulses (or pain sensations) to the brain. Clorphenesin (3-p-chlorophenoxy-1,2-propanediol) is an antigen-associated immunosuppressant: it must be pre-incubated with an antigen to exert its immunosuppressive effect. [1] Injection of the drug and the antigen alone does not inhibit antibody responses. [1] The drug does not destroy or block antigenic determinants, suggesting that it may affect the uptake or intracellular processing of antigens by immune cells. [1] Other studies have shown that it can also inhibit penicillin allergic reactions in guinea pigs and inhibit IgE-mediated histamine release in human leukocytes. [1] |
| Molecular Formula |
C9H11CLO3
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|---|---|
| Molecular Weight |
202.6348
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| Exact Mass |
202.039
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| Elemental Analysis |
C, 53.35; H, 5.47; Cl, 17.49; O, 23.69
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| CAS # |
104-29-0
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| Related CAS # |
104-29-0;
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| PubChem CID |
7697
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
369.5±27.0 °C at 760 mmHg
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| Melting Point |
77-79°C
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| Flash Point |
177.2±23.7 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.565
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| LogP |
1.43
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
13
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| Complexity |
135
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1C([H])=C([H])C(=C([H])C=1[H])OC([H])([H])C([H])(C([H])([H])O[H])O[H]
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| InChi Key |
MXOAEAUPQDYUQM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
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| Chemical Name |
1,2-Propanediol, 3-(4-chlorophenoxy)- (9CI)
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| Synonyms |
NSC-6401; NSC6401; NSC 6401
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 41~100 mg/mL ( 202.33~493.51 mM )
Ethanol : ~41 mg/mL Water : 6.67~10 mg/mL(32.92 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.34 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (12.34 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.9351 mL | 24.6755 mL | 49.3510 mL | |
| 5 mM | 0.9870 mL | 4.9351 mL | 9.8702 mL | |
| 10 mM | 0.4935 mL | 2.4676 mL | 4.9351 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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