STEROID HORMONES

STEROID HORMONE

Compound comprised of a group of cyclical organic

compounds

STEROID HORMONE

Characteristic arrangement of 17 Carbons atoms in a four ring structure linked together from three 6-carbon

rings followed by a 5-carbon ring and an 8-C side chain

CPPP nucleus

(Cyclopentanoperhydrophenanthrene

STEROID HORMONE nucleus present

prednisone

for asthma

as steroidal treatment

may undergo glucuronidation or

sulphation. And most of the time, it may undergo reduction, making it a secondary alcohol.

STEROID HORMONE (SAR)

Position 3

may undergo methylation

STEROID HORMONE (SAR)

Position 6

may undergo reduction

STEROID HORMONE (SAR)

Position 4

may undergo hydroxylation

STEROID HORMONE (SAR)

Position 11

most prone in the addition of compounds

○ steroid hormones differ depending on the substituents attached at position 17.

○ It may undergo esterification, oxidation and

alkylation.

STEROID HORMONE (SAR)

Position 17

5a-Pregnane

nucleus of Progesterone

5a- Androstane

nucleus of Androgen

5a- Estrane

nucleus of Estrogen

Zoosterol

derived from animals

Cholesterol

Zoosterol

Phytosterol

derived from plants

o Ergosterol

o Stigmasterol

Phytosterol

Mycosterol

derived from fungi

testosterone

Androgen

Progesterone

Gestogen

SEX HORMONES

ketone or hydroxyl group

CARDIAC GLYCOSIDES

lactone groups

1. Bufadienolides - contains 6 membered ring

2. Cardenolides - contains 5 membered ring

2 TYPES OF CARDIAC GLYCOSIDES

Cardenolides

contains 5 membered ring

Bufadienolides

contains 6 membered ring

SAPOGENINS

oxacyclic group

used for the commercial synthesis of cortisone, production of

progesterone, and other steroid products

Diosgenin use

Diosgenin

derived from Dioscorea;

SAPOGENINS

are the aglycone, or non-saccharide, portions of the family of natural products known as saponins.

contain steroid or other triterpene

frameworks as their key organic feature

SEX HORMONES

androgen, estrogen and progesterone

Testosterone

Natural androgen

- present in males, also present in females (in small amounts)

- For normal spermatogenesis, development of secondary male characteristics, for growth

ideally, testosterone is used if there is a

decrease level of testosterone in males.

However, it is not mainly used to supply

testosterone levels kasi sa iba na nagagamit.

- Breast Cancer

- Erectile dysfunction

- Growth and development of male sex

organs

Testosterone use

(Androderm)

Testosterone

Available as patch to supply

Testosterone

Low levels of cholesterol - leads to lack of focus, depression, dec muscle mass, man boobs, abdominal fat, dec libido, and dec athletic performance

Androstane

Testosterone nucleus

Adulthood 6-86 ng/dL

Ranges of Normal Testosterone Levels

Adulthood

menopausal

symptoms

Effects of High Testosterone Levels

Adulthood

menopausal

symptoms

Pregnancy 26-309 ng/dL

Ranges of Normal Testosterone Levels

Pregnancy low libido

Pregnancy androgen excess for fetus

Effects of High Testosterone Levels

Pregnancy low libido

Post menopause insulin resistance,

coronary heart disease

Effects of High Testosterone Levels

Post menopause

muscle loss, joint

pain, incontinence

Post menopause 2-41

ng/dL

Ranges of Normal Testosterone Levels

Post menopause

muscle loss, joint

pain, incontinence

At position 3, you may add O

- can be ketone e Add position 7, you may also

add O

SAR: ANDROGEN

O at C3 and C17 - no androgenic activity

5- beta androstane

SAR: ANDROGEN

with androgenic act

5 - alpha androstane

SAR: ANDROGEN

no activity

There should be no chain constriction or extension

SAR: ANDROGEN

abolish activity

if there is a double bond, then it increases anabolic activity

- Double bond = ↑ anabolic activity

SAR: ANDROGEN

At position 1

If it is replaced by the oxygen it can be an oral anabolic activity

- Oxygen at 2 = oral anabolic activity

SAR: ANDROGEN

At position 2

If it is replaced by a pyrazole it improves

anabolic activity

- PYRAZOLE= improved anabolic activity

SAR: ANDROGEN

At position 2 and 3

if there will an addition of OH and addition of

carbonyl agroup (add OH or double bond O it will enhance activity

- OH; Double bond O = Enhance activity

SAR: ANDROGEN

At position 3

if you add halogen itwill increase the activity

- HALOGEN = ↑ anabolic activity

SAR: ANDROGEN

At position 4 and 9

addition of OH = No adrenergic

activity

SAR: ANDROGEN

At position 17

ESTROGEN

Primary female sex hormones

Maintain integrity of skeleton in reproductive age

ESTROGEN function

Stimulation of proliferative phase of

endometrium

ESTROGEN function

ESTROGEN

Development of female reproductive tract and female secondary sex - characters

ESTROGEN

Function: Vasodilation

- Cardioprotection