Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Phenesterine

Phenesterine

Phenesterine structure

Phenesterine 

structure
  • CAS No:

    3546-10-9

  • Formula:

    C39H59Cl2NO2

  • Chemical Name:

    Phenesterine

  • Synonyms:

    Cholest-5-en-3-ol (3β)-,3-[4-[bis(2-chloroethyl)amino]benzeneacetate];Cholesterol,[p-[bis(2-chloroethyl)amino]phenyl]acetate;Cholest-5-en-3-ol (3β)-,4-[bis(2-chloroethyl)amino]benzeneacetate;Acetic acid,[p-[bis(2-chloroethyl)amino]phenyl]-,cholesteryl ester;Phenesterine;Cholesteryl p-bis(2-chloroethyl)aminophenylacetate;NSC-104,469e;Phenesterin;Phenestrin;3β-Hydroxycholest-5-ene [p-[bis(2-chloroethyl)amino]phenyl]acetate;Fenesterin;Fenestrin;NSC 104469;DAL 25;497257-90-6

Description

PHYSICAL DESCRIPTION: White powder. (NTP, 1992)


Phenestrin is a white powder. (NTP, 1992)


Phenestrin is a white powder. (NTP, 1992)|Phenesterin is a steroidal nitrogen mustard with antineoplastic and mutagenic activities. After attachment to cell-surface steroid receptors and uptake, phenesterin enters the nucleus where it alkylates macromolecules, resulting in decreased cell proliferation. (NCI04)

Phenesterine Basic Attributes

644.79700

644.80

34021JC2Z6

104469

DTXSID6021119

C1190

Crystals

Characteristics

29.54000

10.46630

Phenestrin is a white powder. (NTP, 1992)

1.11g/cm3

90-90.5 °C

686.9ºC at 760mmHg

369.2ºC

1.555

less than 1 mg/mL at 68.9° F (NTP, 1992)

Specific optical rotation for D (sodium) line = -13.7 deg

Insoluble in water.

Amines, Phosphines, and Pyridines

PHENESTRIN is an amine and ester.

Safety Information

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicity

A bioassay of phenesterin for possible carcinogenicity was conducted by administering the chemical by gavage to Sprague-Dawley rats and B6C3F1 mice. Groups of 35 rats of each sex were administered phenesterin at one of two doses, either 5 or 10 mg/kg body weight, three times per week for 52 weeks, then observed for an additional 32 or 33 weeks. The vehicle used was 0.05% polysorbate 80 in buffered saline. Controls consisted of groups of 10 rats of each sex which received the vehicle (vehicle control) and 10 rats of each sex which were untreated (untreated control). All surviving rats were killed at 84 or 85 weeks. Groups of 35 mice of each sex were administered the chemical at one of two doses, either 15 or 30 mg/kg body weight, three times per week for 52 weeks. The males receiving 15 mg/kg were observed for an additional period of 29 weeks, and those surviving to this time were then killed; the animals of the remaining groups were observed for additional periods of only 10-22 weeks, due to early deaths. Seventy-seven weeks after the foregoing groups were started, additional groups of 40 mice of each sex were started and were administered the chemical at 7 mg/kg body weight three times per week; administration of the chemical terminated at week 102 for the males and at week 88 for the females, due to deaths of all females at this time. Controls for the low-dose (7 mg/kg) groups of mice consisted of groups of 20 mice of each sex which received the vehicle (vehicle control) and 20 mice of each sex which were untreated (untreated control); controls for the mid-dose (15 mg/kg) and the high-dose (30 mg/kg) controls consisted of groups of 15 mice of each sex similarly receiving the vehicle or untreated. All surviving low-dose controls were killed at 104 weeks, and all surviving mid- and high-dose controls were killed at 81-84 weeks. Phenesterin was toxic to rats and mice at the doses used, as shown by reduced mean body weights and survival. Time-adjusted analyses were used for evaluation of incidences of tumors in the female mice. In female rats, a dose-related trend (P=0.019) was present in adenocarcinoma of the mammary gland, using the pooled controls, and the incidences of the tumor in the individual dosed groups were significant (P<0.009) when compared with those in the pooled controls (controls 1/18, low-dose 12/29, high-dose 12/30). In male mice, the incidence of alveolar/bronchiolar carcinomas or combined alveolar/bronchiolar adenomas and carcinomas in the low-dose group (18/40) was significantly higher (P<0.020) than that in the low-dose vehicle-control group (0/16). In female mice, seven low-dose animals hadalveolar/bronchiolar adenomas and eight other low-dose animals had alveolar/bronchiolar carcinomas. When these tumors were combined, their time-adjusted incidence was significant (P=0.004) when compared with that in the low-dose vehicle controls (controls 1/18, low-dose 15/35). The lower and nonsignificant incidences of these tumors observed in the mid- and high-dose groups may be due to the earlier mortality in these groups compared with the low-dose groups. In each sex of mid- and high-dose mice, incidences of lymphoma and leukemia were dose related (P<0.005), using vehicle controls; they were also significant (P<0.018) in direct comparisons of mid- and high-dose groups of both sexes with respective vehicle controls (males: controls 0/14, mid-dose 9/29, high-dose 11/25; females, time-adjusted: controls 0/15, mid-dose 14/18, high-dose 17/19). The significance of the incidence of lymphoma and leukemia in the mid- and high-dose groups of males was increased (P<0.001) when the pooled-control group was used, both in the test for dose-related trend and in tests for direct comparisons of dosed groups with the controls. In each sex of mice, sarcomas of the myocardium were found in all groups of dosed animals, but in no control animals (males: low-dose 5/40, mid-dose 7/29, high-dose 2/25; females: low-dose 8/34, mid-dose 2/7, high-dose 3/7). In males, the incidence in the mid-dose group was significant when compared with that in the pooled controls (P=0.006); in females, the incidences in the low- and high-dose groups were significant (P<0.023). It is concluded that under the conditions of this bioassay, phenesterin was carcinogenic in female Sprague-Dawley rats, producing adenocarcinomas of the mammary gland, and in both sexes of B6C3F1 mice, producing alveolar/bronchiolar carcinomas, hematopoietic tumors, and myocardial sarcomas.

Drug Information

Antineoplastic

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of chlorine and nitrogen oxides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

fenesterine

Phenesterine Use and Manufacturing

Methods of Manufacturing

Prepd from p-bis(2-chloroethyl)aminophenylacetic acid chloride and cholesterol

Uses

MEDICATION

Computed Properties

Molecular Weight:644.8
XLogP3:12
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:14
Exact Mass:643.3922855
Monoisotopic Mass:643.3922855
Topological Polar Surface Area:29.5
Heavy Atom Count:44
Complexity:969
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.