THIRD AMENDMENT TO REVOLVING CREDIT NOTE AND
FOURTH AMENDMENT TO REVOLVING CREDIT LOAN AGREEMENT

THIS THIRD AMENDMENT TO REVOLVING CREDIT NOTE AND FOURTH AMENDMENT TO REVOLVING
CREDIT LOAN AGREEMENT (this “Amendment”) is entered into as of October 7, 2020,
by and between CUMBERLAND PHARMACEUTICALS INC., a Tennessee corporation
(“Borrower”), and PINNACLE BANK, a Tennessee banking corporation (the “Lender”).
RECITALS:

A.Borrower issued to the order of Lender that certain $12,000,000.00 Revolving
Credit Note dated July 31, 2017, as amended by that certain First Amendment to
Revolving Credit Note and Second Amendment to Revolving Credit Loan Agreement
dated October 17, 2018 whereby among other changes the principal amount thereof
was increased to up to $20,000,000.00, and as amended by that certain Second
Amendment to Revolving Credit Note and Third Amendment to Revolving Credit Loan
Agreement dated May 10, 2019 (the “Note”).

B.Borrower and the Lender entered into that certain Revolving Credit Loan
Agreement dated as of July 31, 2017, as amended by that certain First Amendment
to Revolving Credit Loan Agreement dated August 14, 2018, as amended by that
certain First Amendment to Revolving Credit Note and Second Amendment to
Revolving Credit Loan Agreement dated October 17, 2018 (“Second Amendment to
Loan Agreement”), and as amended by that certain Second Amendment to Revolving
Credit Note and Third Amendment to Revolving Credit Loan Agreement dated May 10,
2019 (the “Loan Agreement”). Capitalized terms not otherwise defined therein
have the same meaning as set forth in the Loan Agreement.

C.Borrower and the Lender desire to amend the Note and Loan Agreement as
provided herein.

NOW, THEREFORE, in consideration of the premises and for other good and valuable
consideration, the receipt and adequacy of which is hereby acknowledged, the
parties hereto agree as follows:

1.The maximum principal amount of the Note, as set forth in the upper right hand
corner of the first page and within the first paragraph thereof, is hereby
decreased by $5,000,000.00 to $15,000,000.00.
2.The fifth paragraph of the Note, regarding repayment, is hereby amended and
restated as follows:

This Note shall be payable as follows: (a) commencing on October 1, 2020 and
continuing on the 1st day of each consecutive month thereafter through and
including September 1, 2022, the Borrower shall pay to the Lender and amount
equal to all accrued and unpaid interest; and (b) this Note shall mature on
October 1, 2022 (the “Maturity Date”), at which time Borrower shall pay to the
Lender an amount equal to all outstanding principal, plus all accrued and unpaid
interest and any other outstanding fees and expenses due and payable under the
Loan Documents.

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3.Borrower acknowledges that as of the date of this Amendment, the current
“Applicable Margin,” as defined within the Note, is 275 basis points per annum.
This Amendment does not contain any revisions to the current definition of
Applicable Margin.

4.All references to the principal amount of the Note, and the Loan amount, set
forth within the Loan Agreement are hereby amended and restated to mean
$15,000,000.00, including without limitation the following: (i) the description
of the Loan in Section 1.1 of the Loan Agreement; and (ii) the definition of
“Note” set forth within Section 9.1 of the Loan Agreement.

5.Section 1.7 of the Loan Agreement is hereby amended and restated as follows:

1.7    Increase of Availability Under Note. Provided that no Default or Event of
Default under the Note exists or is threatened, the Borrower, commencing October
1, 2020, may from time to time request in writing that the Lender increase the
principal amount available under the Note by an aggregate principal amount of up
to an additional $5,000,000.00; provided that the Lender in the exercise of its
sole discretion shall determine whether it will or will not fund any requested
increase. In connection with any request by the Borrower for an increase, the
following shall apply:

a.each approved increase must be in a minimum amount of no less than
$1,000,000.00;

b.no request for an increase shall be delivered to Lender less than ninety (90)
days prior to the Maturity Date;

c.the Borrower’s request to the Lender for an increase shall be made in writing
at least thirty (30) Business Days prior to the date the Borrower desires the
requested increase to be funded and in connection with any such written request
the Borrower shall submit:

i.the purpose for the increase,

ii.Borrower’s calculations, including pro-forma calculations, establishing to
Lender’s satisfaction that none of the financial covenants set forth in the Loan
Documents have been violated, nor will such be violated immediately after any
approved funding, and

iii.Borrower’s certification that all representations and warranties contained
in the Loan Documents are true and correct as of the date of the request, and
that no Default or Events of Default under the Loan Documents exist or are
threatened.

The Lender shall review the request by Borrower for an increase in funding, and
the Lender, in the exercise of its sole discretion, shall determine whether to
approve any request. In the event the Lender elects to fund any requested
increase, Borrower shall:

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(w)    cause the Lender to receive, at Borrower’s expense, satisfactory evidence
that the lien and security interest against the Collateral remains a first
perfected security interest in favor of Lender, subject to no encumbrance
objectionable to Lender;

(x)    cause the Lender to receive all loan documentation required by Lender to
evidence the increase, including without limitation, such loan documentation as
required to insure that all guaranties and security agreements include the
increase;

(y)    pay to Lender all costs and expenses incurred by Lender in connection
with the increase, including, without limitation, indebtedness tax, UCC filing
costs, and attorney fees; and

(z)    pay to Lender a loan fee equal to ten (10) basis points of the amount by
which the Note is increased.

6.Section 6.11 of the Loan Agreement is hereby amended and restated as follows:

6.11     Dividends and Repurchase or Redemption of Stock. Borrower shall not be
permitted to pay dividends or to repurchase or redeem shares of its stock or
that of any Subsidiary except as follows: (i) Borrower may pay dividends and/or
repurchase or redeem such stock in an aggregate amount not to exceed $4,000,000
from October 1, 2020 to the Maturity Date; and (ii) shares net settled for
restricted share vesting up to $300,000 annually shall not count towards the
limitation set forth in item (i).

7.Section 7.5 of the Loan Agreement is hereby amended and restated as follows:

7.6 Liquidity Cure. For a fifteen (15) day period after the occurrence of an
Event of Default under Section 6.7 hereof (such Event of Default being deemed to
have occurred on the date on which the Compliance Certificate for such period is
required to be delivered pursuant to Section 5.1(c) hereof), Borrower may cure
such Event of Default by depositing and maintaining on account with Lender a
cash amount equal to all outstanding Indebtedness hereunder. Borrower may only
exercise the liquidity cure described herein twice during the period from
October 1, 2020 to the Maturity Date.

8.The definition of “EBITDA” set forth within Section 9.1 of the Loan Agreement
is hereby amended to add the following sentence to the end of such definition:
For purposes of calculating EBITDA, EBITDA shall only include EBITDA arising
from a permitted Acquisition if Lender is provided with a quality of earnings
report related to any such Acquisition reasonably acceptable to Lender.

9.The definition of “LIBOR” set forth within Section 9.1 of the Loan Agreement
is hereby amended to add the following sentence to the end of such definition:
Notwithstanding anything herein to the contrary, in no event shall LIBOR be less
than 0.90% per annum.

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10.The definition of “Maturity Date” set forth within Section 9.1 of the Loan
Agreement is hereby amended and restated to mean October 1, 2022.

11.As a condition to the effectiveness of this Amendment, Borrower agrees to pay
all fees and expenses set forth in the Closing Statement executed in connection
with this Amendment.

12.The Note and Loan Agreement are not amended in any other respect.

13.Borrower reaffirms the terms and provisions of the Loan Documents and agrees
that such terms and provisions are valid and binding, enforceable in accordance
with its terms and provisions, subject to no defense, counterclaim, or
objection.

[signatures commence on following page]

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ENTERED INTO as of the date first written above.
BORROWER:
 
CUMBERLAND PHARMACEUTICALS INC.
 

By:/s/ A. J. Kazimi
A.J. Kazimi, Chief Executive Officer

LENDER:
 
PINNACLE BANK
 

By:/s/ Tim BewleyTim Bewley, Senior Vice Presiden

[Signature Page to Second Amendment to Revolving Credit Loan Note and
Third Amendment to Revolving Credit Loan Agreement]