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.
Physicochemical Properties
| Molecular Formula | C9H11CLO3 |
| Molecular Weight | 202.6348 |
| Exact Mass | 202.039 |
| Elemental Analysis | C, 53.35; H, 5.47; Cl, 17.49; O, 23.69 |
| CAS # | 104-29-0 |
| Related CAS # | 104-29-0; |
| PubChem CID | 7697 |
| Appearance | White to off-white solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 369.5±27.0 °C at 760 mmHg |
| Melting Point | 77-79°C |
| Flash Point | 177.2±23.7 °C |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.565 |
| LogP | 1.43 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 13 |
| Complexity | 135 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | ClC1C([H])=C([H])C(=C([H])C=1[H])OC([H])([H])C([H])(C([H])([H])O[H])O[H] |
| InChi Key | MXOAEAUPQDYUQM-UHFFFAOYSA-N |
| 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 |
| Chemical Name | 1,2-Propanediol, 3-(4-chlorophenoxy)- (9CI) |
| Synonyms | NSC-6401; NSC6401; NSC 6401 |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| 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]. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Rapid and complete. Metabolism / Metabolites Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite. Biological Half-Life 2.3-5 hours |
| References |
[1]. Chlorphenesin: an antigen-associated immunosuppressant. Infect Immun. 1970 Jul;2(1):60-4. [2]. Toxicity of the cosmetic preservatives parabens, phenoxyethanol and chlorphenesin on human meibomian gland epithelial cells. Exp Eye Res. 2020 Jul;196:108057. |
| Additional Infomation |
Chlorphenesin is glycerol in which the hydrogen of one of the primary hydroxy groups is substituted by a 4-chlorophenyl group. It has antifungal and antibacterial properties, and is used for treatment of cutaneous and vaginal infections. Its 1-carbamate is used as a skeletal muscle relaxant for the treatment of painful muscle spasm. It has a role as a muscle relaxant, an antibacterial drug and an antifungal drug. It is a glycol, a member of propane-1,2-diols and a member of monochlorobenzenes. A centrally acting muscle relaxant. Its mode of action is unknown. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1203) See also: ... View More ... Drug Indication Used, along with rest and physical therapy, to treat injuries and other painful muscular conditions. Investigated for use in trigeminal neuralgia (tic douloureux), a neuropathic disorder characterized by severe facial pain. Was investigated as a modulator of histamine release. Mechanism of Action The mechanism of action of chlorphenesin is not well defined, and its effects are measured mainly by subjective responses. It is known that chlorphenesin acts in the central nervous system (CNS) rather than directly on skeletal muscle. Pharmacodynamics Chlorphenesin is a muscle relaxant. It blocks nerve impulses (or pain sensations) that are sent to the brain. |
Solubility Data
| 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. 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. 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 corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (12.34 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| 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 |